Thioglycolic Acid → Beta-Propiolactone

HRID 990919Notes

Reaction equation

HRID 990919 reaction equation
[SH:1][CH2:2][C:3]([OH:5])=[O:4].[SH-:6].[Na+:7].Cl[CH2:9][C:10]([O-:12])=[O:11].[Na+]>C(#N)C>[SH:1][CH2:2][CH2:9][C:10]([OH:12])=[O:11].[SH-:6].[Na+:7].[C:3]1(=[O:4])[O:5][CH2:9][CH2:2]1

Participants

7

Reactant 3

HCID 1133Thioglycolic AcidHCID 28015Sodium hydrosulfideHCID 23665759Sodium chloroacetate

Product 3

HCID 2365Beta-PropiolactoneHCID 65143-Mercaptopropionic AcidHCID 28015Sodium hydrosulfide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The acids from which the esters are derived are also generally available commercially but may be made if so desired by procedures of long-standing in the chemical arts. Mercaptoacetic acid, for example, may be made by the reaction of sodium hydro-sulfide with sodium chloroacetate and subsequent acidification. β-mercaptopropionic acid is obtained in about 80% yield from the reaction of sodium hydrosulfide with β-propiolactone in acetonitrile and subsequent acidification. Mercaptosuccinic acid may be made by adding hydrogen sulfide across the double bond of maleic anhydride followed by hydrolysis. Also suitable for the purposes of this invention are the alkyl esters of α-mercapto-propionic acid, which may be prepared from α-chloropropionic acid and sodium thiosulfate according to the procedure described in U.S. Pat. No. 2,413,361.

Sources & evidence

ORD record
ord-41c1e259e0004410898d8ba885a8fa87
Source dataset
uspto-grants-2002_10
Patent number
US06462116B2

Reaction notes

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