Synthesis of 2-chloro-2-phenylacetic acid

Preparation of 2-chloro-2-phenylacetic acid

Preparation of 2-chloro-2-phenylacetic acid

Preparation of 2-chloro-2-phenylacetic acid

0.80 mole of ethyl mandelate is mixed with 0.82 mole of thionyl chloride, and the solution is set aside at room temperature for 16 hours, heated on a water-bath for 30 min, and poured into ice-water. The ethyl 2-chloro-2-phenylacetate is formed in 81-85 % yield, which is extracted several times with ether and, after isolation, is purified by distillation collecting fraction boiling at 98 ºC/1.5 mm. The hydrolysis is performed by a boiling mixture of glacial acetic acid and concentrated hydrochloric acid.

Org. Syn., 36, 3 (1956).

IUPAC Name

2-chloro-2-phenylacetic acid

InChI

InChI=1S/C8H7ClO2/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7H,(H,10,11)

InChI Key

QKSGIGXOKHZCQZ-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)C(C(=O)O)Cl

Depositor-Supplied Synonyms

2-chloro-2-phenylacetic acid, 4755-72-0, Chloro(phenyl)acetic acid, Chlorophenylacetic acid, a-chlorophenylacetic acid, SBB040663, AC1Q3GFD, ACMC-209k9t, AC1L40JG, AC1Q71RB, SCHEMBL664900, A-CHLOROPHENYLACETICACID, Benzeneacetic acid, |A-chloro-, CTK4J0101, alpha-CHLOROPHENYLACETIC ACID, MolPort-001-781-832, QKSGIGXOKHZCQZ-UHFFFAOYSA-N, alpha-chloro-alpha-phenylacetic acid, EINECS 225-284-5, ANW-30543, AR-1I2081, NSC152981, NSC175545, AKOS000268660, AKOS016039394, MCULE-8059678553, NSC-152981, NSC-175545, AK107681, KB-22059, OR043777, OR253681, OR270660, TR-017526, FT-0658317, BENZENEACETIC ACID, A-CHLORO-, (R)-, EN300-21393, B-3563, S01-0457, T5791170

Removed Synonyms

S-2-Chloro-2-phenylacetic acid, CID98950, 2444-36-2, 50508-08-2

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