Thionyl Chloride → p-Tetradecyloxyphenylacetylchloride

HRID 616416Notes

Reaction equation

HRID 616416 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-eba1696c2d1d4425bf72af4a9c007fc0
Source dataset
uspto-grants-1978_02
Patent number
US04073936

Reaction notes

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