(4-Tert-butyloxyphenyl)diphenylsulfonium p-toluenesulfonate → 4-Hydroxyphenyldiphenylsulfonium 4-methylbenzenesulfonate

HRID 1753671Notes

Reaction equation

[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O-:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.C([O:16][C:17]1[CH:22]=[CH:21][C:20]([S+:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)(C)(C)C>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CO>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([O-:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[OH:16][C:17]1[CH:22]=[CH:21][C:20]([S+:23]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 25 g of (4-tert-butyloxyphenyl)diphenylsulfonium p-toluenesulfonate, 0.5 g of p-toluenesulfonic acid monohydrate, and 75 g of methanol was stirred at 80° C. for 5 hours. The reaction solution was cooled to room temperature and concentrated in vacuum, to which 100 g of methylene chloride and 50 g of deionized water were added. The organic layer was separated, washed with water, and concentrated in vacuum. To the concentrate, 100 g of MIBK was added. This was concentrated in vacuum again, obtaining 24 g of the target compound, (4-hydroxyphenyl)diphenylsulfonium p-toluenesulfonate as oily matter. Yield 96%.

Workup

temperatureThe reaction solution was cooled to room temperature
concentrationconcentrated in vacuum, to which 100 g of methylene chloride and 50 g of deionized water
additionwere added
customThe organic layer was separated
washwashed with water
concentrationconcentrated in vacuum
additionTo the concentrate, 100 g of MIBK was added
concentrationThis was concentrated in vacuum again

Sources & evidence

ORD record: ord-ee5ec6ff28964c09a643a41783a085ae
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09164384B2

Reaction notes

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