Thionyl Chloride → p-(1-Methyl-heptyloxy)benzoic acid chloride

HRID 568756Notes

Reaction equation

HRID 568756 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][CH:6]([O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>>[CH3:5][CH:6]([O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([Cl:3])=[O:19])=[CH:16][CH:15]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 13878419p-(1-Methyl-heptyloxy)benzoic acid

Product 1

HCID 13878422p-(1-Methyl-heptyloxy)benzoic acid chlorideYield 93%

Procedure

Thionyl chloride (51.2 g, 0.43 mol) was added to optically active p-(1-methyl-heptyloxy)benzoic acid (90.0 g, 0.36 mol), followed by refluxing the mixture for about 2 hours, thereafter completely removing excess thionyl chloride by distillation under reduced pressure to obtain optically active p-(1-methyl-heptyloxy)benzoic acid chloride (90.0 g).

Workup

  1. temperatureby refluxing the mixture for about 2 hours
  2. distillationcompletely removing excess thionyl chloride by distillation under reduced pressure

Sources & evidence

ORD record
ord-a514f906415d486db0b095e432061e79
Source dataset
uspto-grants-1988_03
Patent number
US04729847

Reaction notes

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