Thionyl Chloride → p-Tetradecyloxyphenylacetylchloride

HRID 596713

Reaction equation

HRID 596713 reaction equation
[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=O)=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].S(Cl)([Cl:28])=O>C1C=CC=CC=1>[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([Cl:28])=[O:25])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10472964p-Tetradecyloxyphenylacetic acid

Product 1

HCID 10021844p-Tetradecyloxyphenylacetylchloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 10.0 g. p-tetradecyloxyphenylacetic acid in 100 ml. absolute benzene is treated with 19.9 g thionylchloride and refluxed for 2.5 hours. The reaction mixture is then evaporated under vacuum (i.v.) and azeotroped several times with benzene to remove residual thionylchloride, to obtain crude p-tetradecyloxyphenylacetylchloride, which may be used in Step E, below, without further refining.

Workup

  1. temperaturerefluxed for 2.5 hours
  2. customThe reaction mixture is then evaporated under vacuum (i.v.)
  3. customazeotroped several times with benzene
  4. customto remove residual thionylchloride

Sources & evidence

ORD record
ord-5e97ab17b6eb4490a02e2bd78e3b8f55
Source dataset
uspto-grants-1977_03
Patent number
US04011339

Linked notes

Loading…