Synthesis of ethyl trifluoroacetate (trifluoroacetic acid ethyl ester)

Preparation of ethyl trifluoroacetate

Preparation of ethyl trifluoroacetate (trifluoroacetic acid ethyl ester)

Preparation of ethyl trifluoroacetate (trifluoroacetic acid ethyl ester)

114 g of trifluoroacetic acid and 138 g of absolute ethanol and 5 ml of concentrated sulfuric acid were added to a 500 ml flask. An efficient reflux condenser was attached and the reaction mixture heated at reflux for 3 hours. The reflux condenser was replaced with a distillation set-up and the final product was distilled by collecting fraction passing around 70° C. The distillate is dried first over CaCl2 and then over Na2SO4, over night. Ethyl trifluoroacetate is purified by fractional distillation yielded 89 grams or 62.5%, with boiling point 59-61°C.

A study of the synthesis of 2-trifluoromethyl pyrimidines, by J. King, 27, 1961

Preparation of ethyl trifluoroacetate

Preparation of ethyl trifluoroacetate

170 g of anhydrous sodium trifluoroacetate are treated with a cold mixture of 140 g of absolute ethanol and 160 g of conc. sulfuric acid. After standing at room temperature for 3 hours, the reaction mixture was heated on a water-bath, and obtained ethyl trifluoroacetate is distilled off during one and one-half hours up to a boiling point of 64° C. The crude ethyl trifluoroacetate is washed once with 100 ml of cold 5% sodium carbonate solution then dried over of calcium chloride at 0° C. Ethyl trifluoroacetate is purified by mixing with 15 g of phosphorus pentoxide and distilling yielding 90% of product boiling at 60-62° C.

J. Am. Chem. Soc., 65 (8), 1458–1460, (1943).

Preparation of ethyl trifluoroacetate from 2,4,6-tris(trifluoromethyl)-1,3,5-triazine

Preparation of ethyl trifluoroacetate from 2,4,6-tris(trifluoromethyl)-1,3,5-triazine

Heating 2,4,6-tris(trifluoromethyl)-1,3,5-triazine with aqueous-ethanolic HCl affords ethyl trifluoroacetate which is mostly collected as an azeotrope, b.p. 52.5-56°, with water; this can be dehydrated by concentrated sulfuric acid or hydrolyzed to sodium trifluoroacetate by sodium hydroxide solution. This salt is powdered and added to concentrated sulfuric acid, and anhydrous trifluoroacetic acid, b.p. 72-74°, is distilled off. Trifluoroacetic acid and water form an azeotrope, b.p. 105.5°, containing 79.4% of the acid.

J. Amer. Chem. Soc, 72, 3527 (1950).

IUPAC Name

ethyl 2,2,2-trifluoroacetate

InChI

InChI=1S/C4H5F3O2/c1-2-9-3(8)4(5,6)7/h2H2,1H3

InChI Key

STSCVKRWJPWALQ-UHFFFAOYSA-N

Canonical SMILES

CCOC(=O)C(F)(F)F

Depositor-Supplied Synonyms

ETHYL TRIFLUOROACETATE, 383-63-1, ethyl 2,2,2-trifluoroacetate, Trifluoroacetic acid ethyl ester, ethyltrifluoroacetate, Trifluoroacetic acid, ethyl ester, Ethyl trifluoroethanoate, Acetic acid, trifluoro-, ethyl ester, Acetic acid, 2,2,2-trifluoro-, ethyl ester, STSCVKRWJPWALQ-UHFFFAOYSA-N, SBB008466, ethyl trifloroacetate, ethyl trifluoroacetat, ethyl triflouroacetate, ethyl tri-fluoroacetate, ethyl trifluoro-acetate, PubChem12576, ACMC-209izs, CF3COOC2H5, UNII-A6TZK6X11X, AC1L1TU4, AC1Q4I8V, A6TZK6X11X, DSSTox_CID_21959, DSSTox_RID_79886, DSSTox_GSID_41959, SCHEMBL60813, E50000_ALDRICH, KSC489Q5T, CHEMBL3185188, CTK3I9859, Trifluoro-acetic acid ethyl ester, MolPort-000-155-396, Ethyl ester of Trifluoroacetic acid, ACT08923, EINECS 206-851-6, Tox21_301309, AN-297, ANW-28886, AR-1J0053, BBL004106, EBD563781, NSC220215, RW2128, STK260851, ZINC01755719, AKOS000119926, FR-2101, LS41250, MCULE-8249948075, NSC 220215, NSC-220215, RP20713, RTR-015509, ZH10004, ethyl-alpha,alpha,alpha-trifluoroacetate, NCGC00255908-01, BC201646, BP-12762, CAS-383-63-1, CJ-07029, CJ-29671, KB-51692, SC-17391, AI3-52221, DB-049273, TR-015509, FT-0625798, ST45021370, T0432, T7776, X7231, 19505-EP2269990A1, 19505-EP2305682A1, 19505-EP2305808A1, 19505-EP2308879A1, 19505-EP2314576A1, 2,2,2-TRIFLUORO-ACETIC ACID ETHYL ESTER, I14-0077, 3B3-017171, InChI=1/C4H5F3O2/c1-2-9-3(8)4(5,6)7/h2H2,1H

Removed Synonyms

trifluoroethyl acetate, Acetic acid, ethyl ester, CID9794, 40323-53-3

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