Thionyl Chloride → 4-Isopropyl-1-methylcyclohexylcarbonyl chloride

HRID 2291726Notes

Reaction equation

HRID 2291726 reaction equation
S(Cl)([Cl:3])=O.[CH:5]([CH:8]1[CH2:13][CH2:12][C:11]([C:15]([OH:17])=O)([CH3:14])[CH2:10][CH2:9]1)([CH3:7])[CH3:6]>>[CH:5]([CH:8]1[CH2:13][CH2:12][C:11]([CH3:14])([C:15]([Cl:3])=[O:17])[CH2:10][CH2:9]1)([CH3:7])[CH3:6]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 133066451-Methyl-4-(propan-2-yl)cyclohexane-1-carboxylic acid

Product 1

HCID 133066464-Isopropyl-1-methylcyclohexylcarbonyl chlorideYield 86.4%

Procedure

An excess of thionyl chloride was added to 10 g of 4-isopropyl-1-methylcyclohexylcarboxylic acid (cis:trans=1:1, b.p.=122° C./2 mm Hg), and the mixture was stirred for 3 hours. The remaining thionyl chloride was distilled off in a vacuum from the resulting reaction mixture, and the oily product obtained was distilled in a vacuum to obtain 9.5 g of 4-isopropyl-1-methylcyclohexylcarbonyl chloride having a boiling point of 150° to 152° C./60 mm Hg. (Yield: 86.4%.)

Workup

  1. distillationThe remaining thionyl chloride was distilled off in a vacuum from the resulting reaction mixture
  2. customthe oily product obtained
  3. distillationwas distilled in a vacuum

Sources & evidence

ORD record
ord-fee85b505eb54873b4bc4dba82cb3de1
Source dataset
uspto-grants-1989_01
Patent number
US04797502

Reaction notes

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