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

HRID 18478

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

Menthane-3-carboxylic acid (54.35 g) was refluxed with 80 ml of thionyl chloride for 3 hours. The SOCl2 was removed by distillation, and the acid chloride was distilled at 114-115° C. (8 Torr). (Lit. b.p. 84-85° C. at 3.5 Torr). Yield: 50 g (84%).

Workup

customThe SOCl2 was removed by distillation
distillationthe acid chloride was distilled at 114-115° C. (8 Torr)

Sources & evidence

ORD record: ord-34d4b82d37d54495b5bc982f2f768f38
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741355B2

Linked notes

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