(4-Chlorophenyl)acetic acid → 4-Chlorophenylacetyl chloride

HRID 258999Notes

Reaction equation

HRID 258999 reaction equation
ClC1C=CC([C:8]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[O:9])=CC=1.[Cl:18]C1C=CC(CC(O)=O)=CC=1>S(Cl)(Cl)=O>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][C:8]([Cl:18])=[O:9])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 15880(4-Chlorophenyl)acetic acidHCID 5873181,2-Bis(4-chlorophenyl)ethanone

Product 1

HCID 906924-Chlorophenylacetyl chloride

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

4,4'-Dichlorodeoxybenzoin can be prepared by heating 4-chlorophenylacetic acid (85g) in thionyl chloride (59.5g) under reflux for 2.5 hours to yield 4-chlorophenylacetyl chloride (45.5g) which is subsequently dissolved in chlorobenzene (30g) and added dropwise with cooling to a stirred aluminium chloride (73g). The resultant mixture is cooled and stirred for a further 0.5 hours and then heated at 100° for one hour. The mixture was again cooled and poured into a mixture of conc. hyrochloric acid (200ml) and ice (1 liter) precipitate on standing crude 4,4'-dichlorodeoxybenzoin which on recrystallisation from methanol has a melting point of 115°-116°.

Workup

  1. temperatureunder reflux for 2.5 hours

Sources & evidence

ORD record
ord-3521165638664a20b5150dd6eaa1973a
Source dataset
uspto-grants-1977_07
Patent number
US04035499

Reaction notes

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