Thionyl Chloride → Cyclohexanecarbonyl chloride, 5-methyl-2-(1-methylethyl)-

HRID 1447836Notes

Reaction equation

[CH:1]1([CH3:13])[CH2:6][CH2:5][CH:4]([CH:7]([CH3:9])[CH3:8])[CH:3]([C:10](O)=[O:11])[CH2:2]1.S(Cl)([Cl:16])=O>>[CH:1]1([CH3:13])[CH2:6][CH2:5][CH:4]([CH:7]([CH3:9])[CH3:8])[CH:3]([C:10]([Cl:16])=[O:11])[CH2:2]1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 97896p-Menthane-3-carboxylic acid

Product 1

HCID 13734319Cyclohexanecarbonyl chloride, 5-methyl-2-(1-methylethyl)-

Procedure

p-Menthane-3-carboxylic acid (1.84 g.), was heated under reflux with thionyl chloride (4 ml.) for 3 hours. The excess of thionyl chloride was then distilled off in vacuo. The crude produce p-menth-3-oyl chloride was dissolved in diethyl ether (25 ml.) and the ethereal solution was added with stirring and cooling to a solution of ethylamine (1.0 ml. of 70% w/s solution in water) and sodium hydroxide (0.4 g.) in water (25 ml.). The mixture was stirred for one hour and the ethereal layer was then separated. The aqueous layer was washed with ether (25 ml.) and the combined ethereal solution was washed with dilute hydrochloric acid and then water. The ether solution was dried (MgSO4) and evaporated to give a white crystalline solid. This solid was recrystallized from acetone: water (9:1) by dissolving the crystals at room temperature and then cooling to produce N-ethyl-p-menthane-3-carboxamide as a white crystalline solid, mp. 82.5°-84.5°.

Workup

distillationThe excess of thionyl chloride was then distilled off in vacuo

Sources & evidence

ORD record: ord-53b5989a66f24f6a8b3530b8ceb52ddc
Source dataset: uspto-grants-1979_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04178459

Reaction notes

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