4-(Trifluoromethyl)benzoic acid → 4-(Trifluoromethyl)benzoyl chloride

HRID 1383230Notes

Reaction equation

HRID 1383230 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=1.C(Cl)(=O)C([Cl:17])=O>CN(C)C=O.C(Cl)Cl>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:17])=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 99664-(Trifluoromethyl)benzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 676074-(Trifluoromethyl)benzoyl chlorideYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 20.0 grams (0.105 mole) of 4-trifluoromethylbenzoic acid and four drops of dimethylformamide in 300 mL of methylene chloride was cooled to 0°-10° C., and 14.7 grams (0.116 mole) of oxalyl chloride was added. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature where it stirred for 18 hours. The reaction mixture was then concentrated under reduced pressure, yielding 21.9 grams of 4-trifluoromethylbenzoyl chloride as a semi-solid. The reaction was repeated.

Workup

  1. additionUpon completion of addition
  2. concentrationThe reaction mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-2c20dc6ec85e43a189dc7f6da8bf139f
Source dataset
uspto-grants-1989_02
Patent number
US04808762

Reaction notes

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