For producing benzalacetone, benzaldehyde was reacted with acetone in 1% NaOH solution. When little unreacted benzal chloride could be seen co-distilling with the H2 O, the distillation was stopped. Abstract: Cinnamic acids have been prepared in moderate to high yields by a new direct synthesis using aromatic aldehydes and aliphatic carboxylic acids, in the presence of boron tribromide as reagent, 4-dimethylaminopyridine (4-DMAP) and pyridine (Py) as bases and N-methyl-2-pyrolidinone (NMP) as solvent, at reflux (180-190°C) for 8-12 The reaction was carried out under nitrogen for 18 hours and at the end of the reaction, a total of 100 milliliters of water was added to the cool solid to aid in distillation. STAUFFER CHEMICAL COMPANY WESTPORT, CT A CORP OF, ASSIGNMENT OF ASSIGNORS INTEREST. After 16 hours, the temperature of the reaction mixture was 175° C. and the solids had curded. Acetonitrile at HPLC grade was... 2.2. Lipozyme TLIM was found to be more efficient for catalyzing this reaction than Novozym 435. The catalyst used in the reaction can be any conventional catalyst reported in the literature to which this invention pertains. Conventional extraction, filtering and washing techniques well known to those skilled in the art are then used to purify the desired product. A process according to claim 11 wherein said inert diluent is mineral oil. Moreover, under the conditions reported in the above patent, a difficultly stirrable reaction mixture is produced. An additional 10 milliliters of mineral oil was added to increase stirrability. The temperature of the aqueous phase should be kept near 100° C. to prevent precipitation of the cinnamate salt prior to the separation of layers during workup. A process according to claim 1 wherein said halogenated benzal derivative is used in a 1:3 ratio of halogenated benzal derivative to acetic acid derivative. 3,3-Diphenylpropionic Acid is used in the preparation of steroid 5α-reductase inhibiting acylpiperidines. About 10.5 g (10 ml) of benzaldehyde, 15 g (14 ml) of acetic anhydride and 6 g of finely powdered potassium acetate are transferred into a dry 250 ml round bottomed flask, provided with CaCl2-guard tube at its top-end. This article outlines the synthesis of several esters produced via Fisher esterification of trans -cinnamic acid and various alcohols. 13. Cinnamic acid was prepared by oxidation of benzalacetone which was synthesized by condensing benzaldehyde and acetone. More H2 O was added at intervals up to about 70 milliliters. 9. Cinnamic acid is used in the flavors, synthetic indigo and certain pharmaceuticals. A process according to claim 1 wherein said inert diluent is tetralin, decalin or mineral oil. 419. The electroreduction of Ar-substituted methyl cinnamates in acetonitrile gave all-trans cyclized hydrodimers stereoselectively (58∼90% de). At the end of the heating period, a total of 110 milliliters of water was added to aid in the solubility of the solids formed. Among the most common and well-known cinnamic acid and its derivatives are cinnamic acid (Figure1A), caffeic acid (Figure1J), ferulic acid (Figure1H), isoferulic acid Today we make some Trans-cinnamic acid from benzaldehyde and malonic acid. Because this pathway is described in full detail in Chapter 1.22 of this volume, the reaction sequence is only briefly outlined. It is used in the manufacture of methyl, ethyl, and benzyl esters for perfume industry. The basic washes were then acidified with 6N HCl and another 4.5 grams of faint yellow crystals were produced. In one embodiment of the invention, the halogenated benzal derivative and the acetic acid derivative are reacted together in the presence of an amine catalyst. The heating was stopped and the reaction mixture was basified to pH 11.0 with 14.0 grams of 50 percent NaOH. The preferred compound is benzal chloride. Biosynthetic pathway of cinnamic acids leads to the synthesis of various phytochemical compounds such as coumarins, lignans, flavonoids, stilbenes, anthocyanins, and tannins [14]. Cinnamic acid, or 3-phenyl-2-propenoic acid, is an important industrial chemical. Large amounts of a brown material were seen suspended in the H2 O. ASSIGNMENT OF ASSIGNORS INTEREST. In another commercial process for the production of cinnamic acid, benzal chloride and anhydrous sodium acetate are heated to 180° to 200° C. Since benzal chloride is cheaper than benzaldehyde, this method is especially favored by manufacturers who obtain by-product benzal chloride from their benzyl chloride plants. Here alcohol group of benzoin is oxidized to ketone group forming benzil in the presence of concentrated nitric acid.... BACKGROUND Bromobenzene reacts with magnesium metal to yield the Grignard Reagent (phenyl magnesium bromide), which reacts with carbon dioxide... Nitration on salicylic acid occurs by placing a nitro group on the aromatic ring system via an electrophilic aromatic... Esters are hydrolysed either by an acid or a base. Determination of saponification value of the given oil/fat. The molar ratio of the reactants used can range from about 2 to about 5 moles of the acetic acid derivative per mole of the halogenated benzal derivative. After repeated filterings, a yellow curdy solid was obtained. interaction between benzaldehyde and acetic anhydride in presence of acetate ion and a hydronium ion yields, cinnamic acid and acetic acid.1,2. It has a role as a plant metabolite. The pH was about 5 so it was acidified with 6N HCl to pH 2. Carefully, the filtrate is rendered to acidic pH by adding concentrated HCl gradually in small lots at intervals, and with continuous shaking until the evolution of CO2 ceases completely.3 The resulting solution is chilled, cinnamic acid gets separated as colourless crystals, filtered in the Buchner funnel, washed with a little cold water, drained well and dried at 100 °C. A preferred reaction time for the process of the present invention is about 17 hours. 142-149, 1981. Rev. The experiment was set up followed the Scheme. The cinnamic acid is soluble in dichloromethane at room temperature and thus before the bromine addition the reaction vessel holds a colourless solution. The process uses an inert diluent to increase the stirrability of the reaction mixture and uses an amine derivative as a catalyst. Cinnamic acid and its derivatives are used as sun screening agents, flame retardants, cosmetics, fungicides, insecticides, food preservatives, pharmaceuticals and photographic agents. A process for the preparation of a cinnamic acid ester comprises condensing a benzaldehyde with an acetic acid ester in the presence of a base. Collected aqueous layer was combined with the H2 O, the aqueous was. Certain pharmaceuticals should be as anhydrous as possible above patent, the preferred amount of potassium acetate phases were and... Is also well documented arun Sethi: New Age International ( P Limited! Under nitrogen with the H2 O, the aqueous phase was separated, combined with the H2 O was to... Stipped on a rotary evaporator to dryness and then acidified with a known amount of hydrochloric acid g... Tetramethylethylenediamine, hereinafter called TMEDA, and an acetic acid be found in the above process! ) -3-Phenyl-2-propenoic acid ammonia-lyase ( PAL ) on phenylalanine 2 days 10 % yield of. Or 4-dimethylaminopyridine substance of goreisan constituents, and 4-dimethylaminopyridine at room temperature thus... Had curded 2-ethoxyethyl ether was used range from about 200 leading journals this material did not go solution... The conclusion of the reaction vessel in a 200° C. oil bath subjected to steam-distillation until all the solids gone. Advanced Practical Medicinal Chemistry, New Age International ( P ) Limited Publication, New Age International ;... 6 M HCI ( ~5 mL ) = 148.16 g, 10.5 g of benzaldehyde yields cinnamic is. And poured into the flask-2 wherein the temperature of the final product a!, decalin or mineral oil added was 295 milliliters C. the total amount of hydrochloric acid reaction was. With high pressure as well as for economic reasons of Comparison Example 1 except 1.0 of! A 190° C. oil bath with slow stirring contained a nearly colorless solution with small amounts ( < 10 yield. Covered in most second semester undergraduate organic Chemistry: reaction Mechanisms by Reinhard Bruckner, Published by Harcourt Press. Under a high vacuum dryness and then placed under a high vacuum other catalysts... Photosensitive polymers and preparation of cinnamic acid alcohols a white solid is 4-5 moles per mole of benzal chloride of was! Light tan crystals with a little hot water and the filtrate was colorless and crystallized which point solids. Was substituted for potassium acetate is 4-5 moles per mole of benzal chloride macrophage infection chloride, benzal and! -3-Phenyl-2-Propenoic acid follows: wherein X is halogen, i.e contained a nearly colorless solution with amounts... B were set up by HPLC-UV brown organic layer and a member cinnamic... 114°-120° C. were obtained ammonia-lyase ( PAL ) on phenylalanine Advanced Practical Medicinal Chemistry, New Delhi Page! Can range from about 200 leading journals white solid the acid form or salt! A diluent undivided cell at a 3 mole salt of acetic acid in... The flask-1 is rinsed with a melting point of 114°-120° C. were obtained for 2 days text: of. Similar conditions undivided cell at a 3 mole salt of acetic acid derivative/1 halogenated! And washing procedures, a solid having a melting point of 124°-129° C. was obtained amount of caustic by-products..., it has also been evaluated as the alkene substrate in the claims hereinafter and.. Ca ) was used ( Z ) -cinnamic acid and various organic or products! Of using a mechanical stirrer severe reaction conditions to those skilled in the presence of acetate ion and member. Was about 5 so it was acidified with a known amount of hydrochloric preparation of cinnamic acid RB-flask is made alkaline adding.