Thioglycerol → 2-(2,3-Dihydroxypropylthio)-3',4',5'-trimethoxyacetophenone

HRID 618083Notes

Reaction equation

[SH:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5].Br[CH2:8][C:9]([C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=1)=[O:10]>>[OH:6][CH:3]([CH2:4][OH:5])[CH2:2][S:1][CH2:8][C:9]([C:11]1[CH:12]=[C:13]([O:21][CH3:22])[C:14]([O:19][CH3:20])=[C:15]([O:17][CH3:18])[CH:16]=1)=[O:10]

Participants

Reactant 2

HCID 7291Thioglycerol

HCID 36857322-Bromo-1-(3,4,5-trimethoxyphenyl)ethanone

Product 1

HCID 218501592-(2,3-Dihydroxypropylthio)-3',4',5'-trimethoxyacetophenoneYield 94.8%

Procedure

Substantially the same procedure as in Reference Example 13 was repeated using 1-mercapto-2,3-propanediol (12.25 g) and 2-bromo-3',4',5'-trimethoxyacetophenone (Compound XIa, 16.39 g) obtained in Reference Example 1 to give 2-(2,3-dihydroxypropylthio)-3',4',5'-trimethoxyacetophenone (Compound IX-13, 17.00 g).

Workup

customobtained in Reference Example 1

Sources & evidence

ORD record: ord-c4a0210276e6436f93e244fa0651ccb0
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05952355

Reaction notes

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