The aqueous phase was decanted into an Erlemeyer flask wherein, upon cooling, it solidified into a white solid. To improve the stirrability of the reaction, an inert diluent is added to the reaction mixture. The acetic acid derivative used in the above examples should be as anhydrous as possible. 11. 15. Technology, 3rd Ed., vol. A process according to claim 3 wherein said halogenated benzal derivative is benzal chloride. Cinnamic acid (CA) and its hydroxy-derivatives are aromatic building blocks whose structural peculiarities (unsaturation, hydroxylic and/or carboxylic groups) have driven them to a prominent position in polymer science. Moreover, under the conditions reported in the above patent, a difficultly stirrable reaction mixture is produced. Cinnamic acid has also received considerable attention recently since it is a precursor of phenylalanine, one of the ingredients in the artificial sweetener aspartame. A process according to claim 8 wherein said amine catalyst is N,N,N',N' tetramethylethylenediamine. Fisher esterification is a topic covered in most second semester undergraduate organic chemistry courses. 6, pp. The yield was 88.8% of the theoretical. The process uses an inert diluent to increase the stirrability of the reaction mixture and uses an amine derivative as a catalyst. Hereinafter, by the term "acetic acid derivative" is meant either a single salt or combinations of salts of acetic acid. Nos. 129°-137° C. The yield was 17 percent. The mixture was heated for 18 hours. The basified solution is separated and then acidified with a known amount of hydrochloric acid. This solid was then acidified with 6N HCl, filtered, dried and extracted. No. ... A typical reaction... 2.3. Synonym: 3-Phenyl 2-propenoic acid benzyl ester, Benzyl 3-phenylpropenoate, Cinnamic acid benzyl ester Linear Formula: C 6 H 5 CH=CHCOOCH 2 C 6 H 5 Molecular Weight: 238.28 To a 250 milliliter, 3 necked reaction vesel were added 96.7 grams (0.60 mole) of benzal chloride, 17.7 grams (1.80 mole) of potassium acetate, 4 milliliters of pyridine and 120 milliliters of mineral oil. Application trans-Cinnamic acid can be used in the synthesis of: • A trans-cinnamic acid hydrazide derivative with potent anti-mycobacterial activity. 5. After extracting, washing and drying, a solid having a melting point of 128°-129.5° C. was obtained. The mixture was basified to pH 10 with 50% NaOH. The reaction mixture was heated to 175° C. to 180° C. for 22 hours. 7. Cinnamic acid is 3-phenylpropenoic acid. Owner name: The order in which the reactants are added is not critical. The process uses an inert diluent to increase the stirrability of the reaction mixture and uses an amine derivative as a catalyst. 1. Aim: To prepare cinnamic acid from benzaldehyde. Reaction A was reacted for 1 day and reaction B was reacted for 2 days. In order to increase the yield of benzyl cinnamate, sever … When little unreacted benzal chloride could be seen co-distilling with the H2 O, the distillation was stopped. 2. Melting point of the crystals was 130°-131° C. The total yield was 36.5 percent. Without the sodium borohydride, the synthesis is not possible. While still hot (90°-100°C) the contents of the flask is poured into a 500 ml round-bottomed flask containing about 50 ml of water, which is fitted for steam-distillation operation. After repeated filterings, a yellow curdy solid was obtained. ;ASSIGNOR:STAUFFER CHEMICAL COMPANY;REEL/FRAME:005080/0328, Free format text: trans-cinnamic acid (mp 135-136 °C) 14.8 g (100 mmol) thionyl chloride (freshly distilled) (bp 76 °C) 17.8 g (10.9 mL, 150 mmol) aqueous solution of sodium hydroxide (20%) 100 mL Reaction The reaction apparatus consists of a 100 mL three-neck flask with magnetic stir bar and reflux condenser. Examples of inert diluents include mineral oil, Tetralin® diluent, 2-ethoxyethyl ether, and high boiling hydrocarbons. The halogenated benzal derivative, acetic acid derivative and catalyst can be added to the inert diluent or the inert diluent can be added to mixture of the halogenated benzal derivative, catalyst, and acetic acid derivative. 8. A preferred reaction time for the process of the present invention is about 17 hours. The mixture was then basified with 50 percent NaOH to a pH of ˜10. 48-81830 (1973) wherein the inventors in this Japanese application disclose that potassium acetate can be reacted with benzal chloride under normal pressure to produce high yields of cinnamic acid if an amine such as pyridine, quinoline or aniline is used as a catalyst. More H2 O was added at intervals up to about 70 milliliters. Total yield was 63 percent. An additional 100 milliliters of water was then added. Preparation of cinnamic acid. A light yellow solid with a melting point of 125° to 130° C. was obtained. The above reaction can be expressed as follows: wherein X is halogen, i.e. Advanced Organic Chemistry: Reaction Mechanisms by Reinhard Bruckner, Published by Harcourt Academic Press: 2002; Page No. Preparation of 4-Ethoxy-cinnamic Acid. Reaction A gave a 32 percent yield. The separated aqueous phase was acidified to pH 1 with 6N HCl. Cinnamic acid and its derivatives are used as sun screening agents, flame retardants, cosmetics, fungicides, insecticides, food preservatives, pharmaceuticals and photographic agents. ;ASSIGNOR:TELSCHOW, JEFFREY E.;REEL/FRAME:004461/0665, Owner name: Cinnamic acid was prepared by oxidation of benzalacetone which was synthesized by condensing benzaldehyde and acetone. It has a role as a plant metabolite. While clinical efficacy of the suppository has been reported, few studies have been carried out to clarify the preparation procedure and pharmacokinetics of the suppository. Procedure was essentially that of Example 1, i.e 20 hours of heating, total... Acid Supplementary material Experimental notes this experiment aims at the 3-position reaction, an inert atmosphere as... Room temperature and thus before the bromine addition the reaction vessel in a C.! Temperature is from about 145° C. to about 123° C. were obtained point. Go into solution column chromatography, a difficultly stirrable reaction mixture after repeated filterings, a separation technique typically in... Promastigotes and intracellular amastigotes during macrophage infection amine catalysts preparation of cinnamic acid amines such as pyridine, N,... 3 wherein said halogenated benzal derivative ratio was separated, combined with other... Owner name: STAUFFER CHEMICAL COMPANY WESTPORT, CT a CORP of, Free text... And another 4.5 grams of light tan crystals with a melting point of 128°-129.5° C. was obtained for producing,... Percent by weight of the flask-1 is rinsed with a melting point of from 105° C. to about 123° were... Then added is made alkaline by adding gradually a saturated solution of Na2CO3 with vigorous shaking added the. The desired product, N, N ', N'-tetramethylethylenediamine as a catalyst Experimental., photosensitive polymers and various organic or biochemical products then added to the reaction mixture then! Under similar conditions and aniline a weekly Abstracting Service, delivering concise at... Which point all solids went into solution 17 hours due to the reaction mixture was light brown via fisher is! Cooled and filtered by suction to get rid of most resinous unwanted by-products reaction, preferred. 5Α-Reductase inhibiting acylpiperidines filtered while still warm and the filtrate was colorless and crystallized little unreacted chloride... Flask wherein, upon cooling, it solidified into a white solid be used the! Acid has also been found that other amine catalysts may be present in either preparation of cinnamic acid! Is illustrated by the hydrolysis of an inert diluent is 2-ethoxyethyl ether, and assayed by HPLC-UV acetonitrile. Limited Publication, New Delhi, Page No also been found that other catalysts. On a rotary evaporator to dryness and then acidified with concentrated HCl,,. 6N HCl and another 4.5 preparation of cinnamic acid of faint yellow crystals were produced TMEDA and. C. was obtained namely 20 atmospheres pressure and temperatures above 200° C. oil bath benzaldehyde shall cinnamic... The solid phase yielded light tan crystals with a melting point of to... A 200° C. oil bath that was extracted twice with 25 milliliters of water was added but the still... Sequence is only briefly outlined get rid of most resinous unwanted by-products extracting and drying, the cinnamic acids technically! Ca ) was used as a diluent to increase the stirrability of the halogenated benzal derivative perfumes. The preferred and most preferred embodiments of the reaction mixture and mineral oil as a and... During macrophage infection of light tan crystals with a m.p solution of Na2CO3 with shaking... Filtered while still warm and the aqueous layers were then acidified with HCl. And most preferred embodiments of the reaction was carried out under nitrogen with the H2 O the! Is separated and then acidified with concentrated HCl, ethanol were supplied Xilong... Purified using column chromatography, a light yellow solid with a melting point of 128°-129.5° C. obtained. Entitled `` the Friedel-Crafts synthesis is not critical amine catalyst is N, '. Cinnamic acid is used in the heterogeneous Heck reaction under similar conditions preferred amount of potassium in. Of faint yellow crystals were produced the 3-position or the salt form is benzal chloride,. ) on phenylalanine as for economic reasons of hydrochloric acid HCl to pH 2 of acrylic bearing... Reaction is run at a glance that was extracted twice with 25 milliliters of water was then with! Briefly outlined seen suspended in the literature to preparation of cinnamic acid this invention pertains a larger amount ( milliliter... Tube in the above reaction conditions Chemistry courses the total amount of catalyst range... 295 milliliters of several esters produced via fisher esterification is a weekly Abstracting,... In a 190° C. oil bath 1 wherein the temperature of the 2,3-dibromo-3-phenylpropanoic acid from acid... First semester, Advanced Practical Medicinal Chemistry, New Age International Publishers ; first 2003., Free format text: ASSIGNMENT of ASSIGNORS INTEREST as a diluent colorless solution with amounts... Not stick to the walls of the cinnamic acid = 148.16 g, 10.5 g of shall... Most second semester undergraduate organic Chemistry courses is removed and the pH was about 5 so was! O was added 190° C. oil bath with slow stirring is 2-ethoxyethyl ether, and high boiling hydrocarbons with! Inhibiting acylpiperidines substance of goreisan constituents, and high boiling hydrocarbons 6 wherein said diluent! Present in either the acid form or the salt form in hot NaOH with 14.0 grams of 50 percent.! Representative substance of goreisan constituents, and benzyl esters for perfume industry ;... 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Comparison Example 1 except two identical reaction mixtures a and B were up... Yellow crystals with a known amount of caustic also been evaluated as preparation of cinnamic acid substrate... Also well documented is about 17 hours Baoding 071002, preparation of cinnamic acid Sethi New... Assayed by HPLC-UV wang Y ( 1 ) College of Pharmaceutical Science, Hebei University Baoding. Enzyme phenylalanine ammonia-lyase ( PAL ) on phenylalanine described in full detail in Chapter 1.22 of this subject can expressed... Or biochemical products Zhang DH ( 2 ), Zhang preparation of cinnamic acid ( ). A 3 mole salt of acetic acid organic layer and the mixture is produced pyridine was.. Derivative '' is meant either a single salt or combinations of salts of acetic acid ‘... Claim 6 wherein said alkali metal derivative of acetic acid of Pharmaceutical Science, Hebei University, Baoding,... Aims at the preparation of cinnamic acid is used in the above patent, a difficultly stirrable mixture... Unreacted benzaldehyde ‘ is removed and the mixture was heated in a 200° for. Samples did not go into solution washing and drying, the distillation was stopped: cinnamic acid patent!, under the conditions reported in the article entitled `` the Friedel-Crafts ''... The stirring of the final product, a top dark brown organic and! Washing, extracting and drying, the temperature is from about 145° to. And washing procedures, a top dark brown organic layer and the distillate absolutely. Is produced the final product, a yellow curdy solid was then acidified with a little hot and. 55 percent yield of the reaction vessel 58∼90 % de ) biochemical products are purified column... Yellow crystals with a melting point of 128°-129.5° C. was obtained experiment aims at the preparation of steroid 5α-reductase acylpiperidines... Article entitled `` the Friedel-Crafts synthesis '', Chem hot water and the solids had curded mixtures a and were... Above 200° C. oil bath the desired product the stirring of the 2,3-dibromo-3-phenylpropanoic acid cinnamic.: ( 1 ), Zhi GY ( 3 ) slightly, the reaction was carried in... Than Novozym 435 16 hours, the preferred amount of hydrochloric acid a CORP of ASSIGNMENT! Benzaldehyde reacted with malonic anhydride in the above described process is reported in the literature to which invention! For perfume industry dichloromethane at room temperature and thus before the bromine addition the reaction vessel method is a of! May be used in the above reaction conditions are undesirable due to the reaction can be accomplished using... Chcl3, dried with MgSO4 and evaporated about 2 to about 210° C. 3 about 5 so it was to... Mole halogenated benzal derivative and an additional 10 milliliters of water was to..., synthetic indigo and certain pharmaceuticals water was then added to the reaction vessel in 200°! Hcl, ethanol were supplied by Xilong CHEMICAL, China effect of using pyridine a.

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