Water → Phenacyltetrahydrothiophenium bromide

HRID 556239Notes

Reaction equation

HRID 556239 reaction equation
[CH2:1]([Br:10])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].[S:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.O.C(OCC)C>[N+](C)([O-])=O>[Br-:10].[CH2:1]([S+:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 1127TetrahydrothiopheneHCID 3283Diethyl EtherHCID 6259Phenacyl bromide

Product 1

HCID 11346720Phenacyltetrahydrothiophenium bromide

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

88.2 g (0.44 mole) of phenacyl bromide and 39.1 g (0.44 mole) of tetrahydrothiophene were dissolved in 220 g of nitromethane, which was stirred for 4 hours at room temperature. 800 g of water and 400 g of diethyl ether were added to the reaction solution whereupon the mixture separated into two layers. The aqueous layer was taken out, which was an aqueous solution of the target compound, phenacyltetrahydrothiophenium bromide.

Workup

  1. customseparated into two layers

Sources & evidence

ORD record
ord-40e1e37604244a699cdf4239eb6881f8
Source dataset
uspto-grants-2011_11
Patent number
US08057985B2

Reaction notes

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