ChemicalBook CAS DataBase List 3-(Trifluoromethyl)cinnamic acid

3-(Trifluoromethyl)cinnamic acid synthesis

6synthesis methods

Product Name:3-(Trifluoromethyl)cinnamic acid
CAS Number:779-89-5
Molecular formula:C10H7F3O2
Molecular Weight:216.16

To a suspension of m-trifluoromethyl-α-bromohydrocinnamic acid, isopropanol (1.42 1) and benzyltriethylammonium chloride (10.85g), aqueous sodium hydroxide (340 ml, 56%) was added slowly. The temperature was raised to 55-60℃, stirred for 7 hours, and isopropanol was removed in vacuo. Water (500ml) was added to the reaction mass, stirred, cooled to 0℃, and acidified with hydrochloric acid (450ml). The solid was filtered, washed with water, and dried in vacuo at 5O℃ to afford 204g of 3-(Trifluoromethyl)cinnamic acid.

141-82-2 Synthesis

141-82-2
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$5.00/25g

454-89-7 Synthesis

454-89-7
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$14.00/25g

779-89-5
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$9.00/1g

Yield:779-89-5 89%

Reaction Conditions:

with piperidine;pyridine at 110;

Steps:

1 S1.2.1. General Procedure for synthesis of Cinnamic acids (2, 15a to 15s)

General procedure: To a solution of pyridine (3 vol), was added aldehyde (1 mmol) malonic acid (2 mmol)followed by catalytic amount of piperidine (0.1 mmol). The reaction mass was slowly heatedto 110 0C and maintained for 10 - 12 hr at 110 0C. Reaction was monitored by TLC. Reactionmass was cooled to room temperature and quenched into 10 vol of water of pyridine. To thequenched mass was added, NaOH (2 mmol). Reaction mixture was stirred to obtain clearsolution. Then reaction mixture was washed with ethyl acetate (20 vol X 2). Aqueous layerwas then acidified with 50 % sulfuric acid till pH 2.The precipitated solid was filtered andwashed with water (5 vol X 2) followed by pet ether wash 2 vol. The product was suck driedon buchner funnel for 15 min to 60 min. The solid product was dried in oven at 50 to 60 °Covernight. Cinnamic acids were obtained in 80 - 90 % yield.

References:

Atmaram Upare, Abhay;Gadekar, Pradip K.;Sivaramakrishnan;Naik, Nishigandha;Khedkar, Vijay M.;Sarkar, Dhiman;Choudhari, Amit;Mohana Roopan [Bioorganic Chemistry,2019,vol. 86,p. 507 - 512] Location in patent:supporting information