Diphenylacetyl Chloride

[1871-76-7]  · C14H11ClO  · Diphenylacetyl Chloride  · (MW 230.70)

(preparation of diphenylketene1)

Physical Data: mp 49-53 °C; bp 175-176 °C/17 mmHg.

Form Supplied in: 90% technical grade.

Preparative Method: by the action of Thionyl Chloride on diphenylacetic acid.2

Handling, Storage, and Precautions: corrosive; a lachrymator. Use in a fume hood.

Diphenylacetyl chloride is used as the principal reagent in the preparation of diphenylketene.1 Diphenylacetyl chloride reacts with Triethylamine in an inert solvent such as ether or benzene, at rt, to give 53-57% yield of diphenylketene (eq 1). The ketene may be isolated for subsequent use (eq 2).2 More frequently, diphenylketene is generated in situ (eq 3).3

Diphenylacetyl chloride has been used in the synthesis of thiol esters via thiolate ions supported on the anion exchanger Amberlyst A-26. Many acid chlorides have been reacted in this manner (eq 4).4

1. Taylor, E. C.; McKillop, A.; Hawks, G. H. OS 1972 52, 36.
2. Losse, G.; Demuth, E. CB 1961, 94, 1762.
3. Schweizer, E. E.; Evans, S. JOC 1978, 43, 4328.
4. Cainelli, G.; Contento, M.; Manescalchi, F.; Plessi, L.; Panunzio, M. G 1983, 113, 523.

Regina Zibuck

Wayne State University, Detroit, MI, USA

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