Potassium Carbonate → 4-((3,4,5-Trimethoxybenzyl)thio)phenol

HRID 357705

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH2:20]Br>CN(C)C=O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:20][C:19]2[CH:22]=[C:23]([O:27][CH3:28])[C:24]([O:25][CH3:26])=[C:17]([O:16][CH3:15])[CH:18]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-Hydroxy thiophenol (12 g, 0.095 mol) and potassium carbonate (15.86 g, 0.115 mol) were dissolved in 250 ml of N,N-dimethylformamide, and cooled to 0° C. To the above solution at 0° C. was added dropwise 25 g (0.095 mol) of 3,4,5-trimethoxybenzyl bromide prepared in step (1) dissolved in 50 ml N,N-dimethylformamide. After stirring for 2 hr, the ice-bath was removed, and the solution was stirred overnight. The whole solution was poured into water, and extracted with 300 ml ethyl acetate. The organic layer was washed twice with 300 ml of water. Drying over magnesium sulfate, filtration, concentration, and chromatographic purification on silica gel column (ethyl acetate/n-hexane=2/3) gave 20 g (yield 68%) of 3,4,5-trimethoxybenzyl 4-hydroxyphenyl thioether as a white solid.

Workup

customthe ice-bath was removed
stirringthe solution was stirred overnight
additionThe whole solution was poured into water
extractionextracted with 300 ml ethyl acetate
washThe organic layer was washed twice with 300 ml of water
dry with materialDrying over magnesium sulfate, filtration, concentration, and chromatographic purification on silica gel column (ethyl acetate/n-hexane=2/3)

Sources & evidence

ORD record: ord-577d302a667c416aaa4696872b29ad7f
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840991

Linked notes

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