4-(Octyloxy)benzoic acid → 4-Octyloxybenzoyl chloride

HRID 2352136Notes

Reaction equation

HRID 2352136 reaction equation
[CH2:1]([O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].O=S(Cl)[Cl:21]>>[CH2:1]([O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([Cl:21])=[O:15])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

3

Reactant 2

HCID 172314-(Octyloxy)benzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 27602504-Octyloxybenzoyl chloride

Procedure

20 ml of SOCl2 was added to 4.0 g (1.6×10-2 mol) of 4-octyloxybenzoic acid, and the mixture was refluxed under heating for 4 hours. Excessive SOCl2 was distilled off to obtain 4-octyloxybenzoic acid chloride. 3.136 g (1.6×10-2 mol) of 4-(2'-methylbutyloxy)benzenethiol and 1.246 g of pyridine were dissolved in 12 ml of toluene, cooled with ice, and the 4-octyloxybenzoic acid chloride dissolved in 10 ml of toluene was added thereto. The mixture was left standing at 5° C. for 45 min, followed by stirring for 3.5 hours at room temperature.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 4 hours
  3. distillationExcessive SOCl2 was distilled off

Sources & evidence

ORD record
ord-dd6ee067758643e3a9a7363304429a98
Source dataset
uspto-grants-1989_10
Patent number
US04876027

Reaction notes

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