Synthesis of phenylacetyl chloride

Preparation of phenylacetyl chloride

Preparation of phenylacetyl chloride

Preparation of phenylacetyl chloride

8.1 g of oxalyl chloride in 20-30 ml of dry benzene were added in a flask with a ground glass connection fitted to a condenser. To this flask 10 g of the dry sodium phenylacetate added through a funnel. With each addition of phenylacetate there was a vigorous reaction, and hydrogen chloride gas evolved. After all the sodium phenylacetate had been added, the reaction mixture was gently refluxed for two hours. The sodium chloride and unchanged sodium phenylacetate was then filtered off and the filtrate distilled to remove the benzene and finally the phenylacetyl chloride. 7 g of phenylacetyl chloride was obtained with boiling point 125-130° C at 40 mm of Hg. According to the literature 100.5° C at 17 mm of Hg. The yield phenylacetyl chloride 71 %.

Oxalyl chloride and oxalyl bromide as reagents in organic chemistry, L.H. Ulich, 25-26, 1918

Preparation of phenylacetyl chloride

Preparation of phenylacetyl chloride

Phenylacetic acid (0.5 mole) and phosphorus trichloride (0.25 mole) are heated on a steam-bath for an hour. Dry benzene (400 ml) is added to the warm mixture and the benzene solution of phenylacetyl chloride is decanted from the deposited phosphorous acid. Benzene is removed and phenylacetyl chloride is distilled in vacuum  collecting fraction boiling at 125-130° C/40 mm of Hg.

Org. Syn., Coll. Vol. II, 156 (1943).

IUPAC Name

2-phenylacetyl chloride

InChI

InChI=1S/C8H7ClO/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2

InChI Key

VMZCDNSFRSVYKQ-UHFFFAOYSA-N

Canonical SMILES

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

Depositor-Supplied Synonyms

PHENYLACETYL CHLORIDE, Benzeneacetyl chloride, 103-80-0, 2-phenylacetyl chloride, phenyl acetyl chloride, Acetyl chloride, phenyl-, VMZCDNSFRSVYKQ-UHFFFAOYSA-N, EINECS 203-146-5, UN2577, AI3-23871, Phenacetyl chloride, Phenylacetylchloride, benzenacetyl chloride, phenyl acetylchloride, phenylacetyl-chloride, phenyl-acetyl chloride, benzyl carbonyl chloride, 2-phenyl acetyl chloride, 2-phenyl-acetyl chloride, 2-phenylethanoyl chloride, AC1Q5HDG, AC1L1PB6, AC1Q3G9T, SCHEMBL1493, ACMC-1C8V0, UNII-T30899DRND, P16753_ALDRICH, .alpha.-Phenylacetyl chloride, KSC181I7J, CCRIS 8623, T30899DRND, 77830_FLUKA, CTK0I1474, EBD6962, MolPort-000-871-695, BB_SC-6754, ANW-14975, AR-1L0603, BBL011387, SBB040622, STL146489, ZINC02041141, AKOS000268752, MCULE-9204048837, RP21899, RTR-000882, UN 2577, CJ-07665, CJ-32519, P857, SC-78877, Phenacetyl chloride; Benzeneacetyl chloride, DB-032093, LS-188101, TR-000882, FT-0613320, P0129, ST50214049, Phenylacetyl chloride [UN2577] [Corrosive], Phenylacetyl chloride [UN2577] [Corrosive], 105292-EP2270006A1, 105292-EP2287155A1, 105292-EP2292619A1, 105292-EP2298779A1, 3B4-1079, I01-1990, InChI=1/C8H7ClO/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H

Removed Synonyms

Phenylacetic acid chloride, PHENYLACETIC CHLORIDE, CID7679, 88252-77-1

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