Thioglycolic Acid → Beta-Propiolactone

HRID 1735421Notes

Reaction equation

HRID 1735421 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-mercaptopropionic 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, which is incorporated herein by reference.

Sources & evidence

ORD record
ord-29a8dcda03194cf0b8dcf6077e7eb2b8
Source dataset
uspto-grants-1996_07
Patent number
US05536767

Reaction notes

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