Water → (E)-1-phenyl-8-p-toluenesulfonyloxy-2-octene

HRID 477009Notes

Reaction equation

[C:1]1(/[CH:7]=[CH:8]/[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.O.CCOCC>N1C=CC=CC=1>[C:1]1([CH2:7]/[CH:8]=[CH:9]/[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][S:22]([C:19]2[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=2)(=[O:24])=[O:23])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 10 °C

Procedure

To a solution of 7.5 g of (E)-8-phenyl-7-octen-1-ol dissolved in 60 ml of pyridine, 9.1 g of p-toluenesulfonyl chloride was added at 0° C. After stirring at 10° C. for 5 hours, 10 ml of water was added and the mixture was stirred for 30 minutes, followed by addition of 200 ml of ether. The mixture was washed with 10% aqueous hydrochloric acid, water and saturated saline water. The organic layer was dried, and the solvent was removed under reduced pressure. The pale yellow oily product obtained was purified by silica gel column chromatography (solvent: hexane-ethyl acetate=5:1) to give 12 g of (E)-1-phenyl-8-p-toluenesulfonyloxy-2-octene as an oily product.

Workup

stirringthe mixture was stirred for 30 minutes
washThe mixture was washed with 10% aqueous hydrochloric acid, water and saturated saline water
customThe organic layer was dried
customthe solvent was removed under reduced pressure
customThe pale yellow oily product obtained
customwas purified by silica gel column chromatography (solvent: hexane-ethyl acetate=5:1)

Sources & evidence

ORD record: ord-a58846be46a041d9acbe04c68d658a67
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04886817

Reaction notes

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