Thionyl Chloride → 4-(Chlorocarbonyl)phenyl hexanoate

HRID 1632915Notes

Reaction equation

HRID 1632915 reaction equation
[C:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=1)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].S(Cl)([Cl:20])=O>C1(C)C=CC=CC=1>[C:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([Cl:20])=[O:14])=[CH:11][CH:10]=1)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 200636454-(Hexanoyloxy)benzoic acid

Product 1

HCID 126805724-(Chlorocarbonyl)phenyl hexanoateYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 10 g of the resultant 4-hexanoyloxybenzoic acid, 8 g thionyl chloride and 100 ml toluene was stirred and externally heated to be refluxed for three hours. After distilling off the toluene from the mixture, the residue was distilled under reduced pressure to give 8.8 g 4-hexanoyloxybenzoic acid chloride in 82% yield based upon the amount of the 4-hexanoyloxybenzoic acid.

Workup

  1. temperatureexternally heated
  2. temperatureto be refluxed for three hours
  3. distillationAfter distilling off the toluene from the mixture
  4. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-ccf83df1dfea44009fa0983dc7eb010d
Source dataset
uspto-grants-1984_10
Patent number
US04478741

Reaction notes

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