Methyl p-toluenesulfonate → Methyltriphenylphosphonium p-toluenesulfonate

HRID 1904485Notes

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.[S:20]([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)([O:23][CH3:24])(=[O:22])=[O:21]>>[S:20]([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)([O-:23])(=[O:22])=[O:21].[CH3:24][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 6645Methyl p-toluenesulfonate

HCID 11776Triphenylphosphine

Product 1

HCID 18401301Methyltriphenylphosphonium p-toluenesulfonateYield 98.7%

Procedure

A mixture of 11.8 g (45.0 mmol) of triphenylphosphine and 8.40 g (45.1 mmol) of methyl tosylate was allowed to react for 2 hr at 130° C. A total of 19.9 g (44.4 mmol, 98.6%) of methyltriphenylphosphonium tosylate was obtained. This was further purified by stirring overnight in 95:5 ether-acetonitrile. Analyses: mp 147.0°-149.0° C.

Workup

customto react for 2 hr at 130° C

Sources & evidence

ORD record: ord-6a96b3062b9f47d1b293cefda94dddd6
Source dataset: uspto-grants-1989_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04837392

Reaction notes

Loading…