Thionyl Chloride → 3-Ethylcyclobutanecarboxylic acid chloride

Reaction equation

[CH2:1]([CH:3]1[CH2:6][CH:5]([C:7]([OH:9])=O)[CH2:4]1)[CH3:2].S(Cl)([Cl:12])=O>>[CH2:1]([CH:3]1[CH2:6][CH:5]([C:7]([Cl:12])=[O:9])[CH2:4]1)[CH3:2]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 47796Cyclobutanecarboxylic acid, 3-ethyl-

Product 1

HCID 450812713-Ethylcyclobutanecarboxylic acid chlorideYield 60.6%

Procedure

A mixture of 3.3 g (0.027 mole) of 3-ethylcyclobutanecarboxylic acid (prepared in 1E) and 9.4 g (5.7 ml, 0.080 mole) of thionyl chloride was prepared and allowed to stir at room temperature for about 15 hr. Excess thionyl chloride was removed by distillation at atmospheric pressure. The residue was distilled at reduced pressure to yield 2.4 g of the title compound having the following physical characteristics:

Workup

customwas prepared
customExcess thionyl chloride was removed by distillation at atmospheric pressure
distillationThe residue was distilled at reduced pressure

Sources & evidence

ORD record: ord-bd5aa059603b4de884c3fae56ebe28c3
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04220795

Reaction notes

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