Acetic Acid → 4-((3,4,5-Trimethoxybenzyl)sulfinyl)phenol

HRID 357707

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)=[CH:4][CH:3]=1.C(O)(=[O:24])C>O.[O-2].[O-2].[O-2].[Cr+6]>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)=[O:24])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

3,4,5-Trimethoxybenzyl 4-hydroxyphenyl thioether (500 mg, 1.63 mmol), prepared as described in Example 1, was dissolved in 10 mlof acetic acid, and heated to 80° C. A solution of chromium trioxide in 30 ml of distilled water was added dropwise to the above solution. The mixture was stirred for 30 min, cooled to room temperature, diluted with 20 ml of water, and then extracted with 30 ml of ethyl acetate. The organic layer was dried over magnesium sulfate, concentrated and purified on silica gel column chromatography (ethyl acetate/n-hexane=1/4) to give 348 mg (66% yield) of 3,4,5-trimethoxybenzyl 4-hydroxyphenyl sulfoxide as a white powder.

Workup

temperaturecooled to room temperature
extractionextracted with 30 ml of ethyl acetate
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated
custompurified on silica gel column chromatography (ethyl acetate/n-hexane=1/4)

Sources & evidence

ORD record: ord-e92c83b6fc5c41b6952ad2903c7a142b
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840991

Linked notes

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