Thionyl Chloride → Benzoyl chloride, 2,5-bis(2,2,2-trifluoroethoxy)-

HRID 1973191Notes

Reaction equation

HRID 1973191 reaction equation
[F:1][C:2]([F:21])([F:20])[CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:10][C:6]=1[C:7](O)=[O:8].S(Cl)([Cl:24])=O>CN(C)C=O>[F:1][C:2]([F:21])([F:20])[CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:10][C:6]=1[C:7]([Cl:24])=[O:8]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 27360782,5-bis(2,2,2-trifluoroethoxy)benzoic Acid

Product 1

HCID 11427683Benzoyl chloride, 2,5-bis(2,2,2-trifluoroethoxy)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

To 9.4 g. (30 mmoles) of 2,5-di-(2,2,2-trifluoroethoxy)benzoic acid are added 2 drops of dimethylformamide and 7.2 ml. (11.9 g., 100 mmoles) of purified thionyl chloride. The product is refluxed for 3 hours and excess thionyl chloride is removed in vacuo (steam bath/water aspirator pressure). Last traces of thionyl chloride are removed by similar vacuum distillation with added benzene. The product is 2,5-di-(2,2,2-trifluoroethoxy)benzoyl chloride according to infrared spectral measurement.

Workup

  1. temperatureThe product is refluxed for 3 hours
  2. customexcess thionyl chloride is removed in vacuo (steam bath/water aspirator pressure)
  3. customLast traces of thionyl chloride are removed by similar vacuum distillation with added benzene

Sources & evidence

ORD record
ord-570dd2dc1f2b447b8c3adfa6a4823c9c
Source dataset
uspto-grants-1976_12
Patent number
US03996280

Reaction notes

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