Thionyl Chloride → 1-(2,2,2-Trifluoroethoxy)-2-naphthoyl Chloride

HRID 1973190Notes

Reaction equation

HRID 1973190 reaction equation
[F:1][C:2]([F:19])([F:18])[CH2:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[C:15](O)=[O:16].S(Cl)([Cl:22])=O>CN(C)C=O>[F:1][C:2]([F:19])([F:18])[CH2:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[C:15]([Cl:22])=[O:16]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 214931531-(2,2,2-Trifluoroethoxy)-2-Naphthoic Acid

Product 1

HCID 214931501-(2,2,2-Trifluoroethoxy)-2-naphthoyl Chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 10 g. (37 mmoles) of 1-(2,2,2-trifluoroethoxy)-2-naphthoic acid, 21.8 ml. (35.7 g., 300 mmoles) of purified thionyl chloride and 3 drops of dimethylformamide is refluxed for one hour. Excess thionyl chloride is removed in vacuo at water aspirator pressure while heating on a steam bath. Last traces of thionyl chloride are removed by vacuum distillation with added benzene. The product is 1-(2,2,2-trifluoroethoxy)-2-naphthoyl chloride according to infrared spectral measurement.

Workup

  1. additionA mixture of 10 g
  2. customExcess thionyl chloride is removed in vacuo at water aspirator pressure
  3. temperaturewhile heating on a steam bath
  4. customLast traces of thionyl chloride are removed by vacuum distillation with added benzene

Sources & evidence

ORD record
ord-afc3b72f7eb447d487f21eface9e9990
Source dataset
uspto-grants-1976_12
Patent number
US03996280

Reaction notes

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