Thionyl Chloride → p-Tetradecyloxyphenylacetylchloride

HRID 2398158Notes

Reaction equation

HRID 2398158 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-ff1e8e7dff1b4083a8a743fd1ba3079f
Source dataset
uspto-grants-1977_05
Patent number
US04024182

Reaction notes

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