Thionyl Chloride → 4-Chloro-ε-oxobenzenehexanoyl chloride

HRID 1658889Notes

Reaction equation

HRID 1658889 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([CH2:8][CH2:9][CH2:10][CH2:11][C:12](O)=[O:13])=[O:7])=[CH:4][CH:3]=1.S(Cl)([Cl:19])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([Cl:19])=[O:13])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 219395716-(4-Chlorophenyl)-6-oxohexanoic acid

Product 1

HCID 135988994-Chloro-ε-oxobenzenehexanoyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-(4-Chlorobenzoyl)pentanoic acid (9.6g) was dissolved in dry toluene (80 ml) and thionyl chloride (10 ml) added. The reaction mixture was heated to reflux for 4 hours. The excess toluene and thionyl chloride were removed in vacuo, more toluene was added and again removed in vacuo affording 5-(4-chlorobenzoyl)pentanoyl chloride (10.4g 100%) as a pale brown solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. customThe excess toluene and thionyl chloride were removed in vacuo, more toluene
  4. additionwas added
  5. customagain removed in vacuo

Sources & evidence

ORD record
ord-64a5c73ace12424abcd9badbd8c3a7de
Source dataset
uspto-grants-1976_06
Patent number
US03966783

Reaction notes

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