Thionyl Chloride → Benzoyl chloride, 4-(hexyloxy)-

HRID 364854Notes

Reaction equation

HRID 364854 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>>[CH2:5]([O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([Cl:3])=[O:17])=[CH:14][CH:13]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 708344-(Hexyloxy)benzoic acid

Product 1

HCID 170235Benzoyl chloride, 4-(hexyloxy)-Yield 98%

Procedure

Thionyl chloride (485 g of 98%, 4.00 mol) was added dropwise to 300 g (1.35 mol) of 4-hexyloxybenzoic acid. The resulting mixture was refluxed under nitrogen for 2 hours. Distillation yielded 318 g (98%) of 4-hexyloxybenzoyl chloride [boiling point 149°-153° C. (7.5 mm)].

Workup

  1. temperatureThe resulting mixture was refluxed under nitrogen for 2 hours
  2. distillationDistillation

Sources & evidence

ORD record
ord-37bb1f97559e446dbcf78a51799a51db
Source dataset
uspto-grants-1986_08
Patent number
US04606838

Reaction notes

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