Methyl benzenesulfonate → Methyl(triphenyl)phosphanium benzenesulfonate

HRID 1904487Notes

Reaction equation

[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20]1([S:26]([O:29]C)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[C:20]1([S:26]([O-:29])(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH3:20][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

Reactant 2

HCID 6630Methyl benzenesulfonate

HCID 11776Triphenylphosphine

Product 1

HCID 20039293Methyl(triphenyl)phosphanium benzenesulfonateYield 173.5%

Procedure

A mixture of 19.2 g (73.2 mmol) of triphenylphosphine and 12.6 g (73.2 mmol) of methyl benzenesulfonate was allowed to react for 2 hr at 130° C. A total of 27.6 g (63.5 mmol, 86.8%) of the product was obtained after recrystallization from 75:25 toluene-acetonitrile. Analyses: mp 147.6°-149.7° C.

Workup

customto react for 2 hr at 130° C

Sources & evidence

ORD record: ord-1eeb52cc56ab4702a4ecb9a2ffa989a2
Source dataset: uspto-grants-1989_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04837392

Reaction notes

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