Thionyl Chloride → Oxane-4-carbonyl chloride

HRID 1656149Notes

Reaction equation

HRID 1656149 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=O)[CH2:3][CH2:2]1.S(Cl)([Cl:12])=O>>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([Cl:12])=[O:9])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 219302Oxane-4-carboxylic acid

Product 1

HCID 2795505Oxane-4-carbonyl chloride

Procedure

The tetrahydropyran-4-carboxylic esters II required for the novel reaction can be obtained from diethyl tetrahydropyran-4,4-dicarboxylate (i. Chem. Soc. (1952), page 2268). The tetrahydropyran-4-carboxylic esters of the formula II can be obtained from the diethyl ester by hydrolysis using potassium hydroxide to give tetrahydropyran-4,4-dicarboxylic acid, subsequent thermal decarboxylation to give tetrahydropyran-4-carboxylic acid, subsequent reaction with thionyl chloride to give tetrahydropyran-4-carbonyl chloride and subsequent esterification with alcohols (J. Chem. Soc. (1930), p. 2525).

Workup

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Sources & evidence

ORD record
ord-7b913971edcc4f248f81514c0371b935
Source dataset
uspto-grants-1993_10
Patent number
US05252755

Reaction notes

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