Reaktion #60674

ord-f7c0cf0c691042ad8dc440d4807c84dd

Reaktionsgleichung

Cc1ccc(S(=O)[O-])cc1.O.O.[Na+]
sodium p-toluensulfinate dihydrate
CC(C)=O.O.c1ccccc1
water benzene acetone
CC(=O)CCl
chloroacetone
→
CC(=O)CS(=O)(=O)c1ccc(C)cc1
title product
Ausbeute 95.0%
CC(=O)CS(=O)(=O)c1ccc(C)cc1
1-(Toluene-4-sulfonyl)-propan-2-one
Ausbeute 95.0%

Edukte

—
n-tetrabutylammonium bromide
—
( 8 )
Cc1ccc(S(=O)[O-])cc1.O.O.[Na+]
sodium p-toluensulfinate dihydrate
CC(C)=O.O.c1ccccc1
water benzene acetone
CC(=O)CCl
chloroacetone

Reagenzien

Keine

Lösungsmittel

CCCCCCC.CCOC(C)=O
ethyl acetate n-heptane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeWas prepared

Vorschrift

Was prepared according to Crandall et al. J. Org. Chem. 1985, (8) 50, 1327-1329 from sodium p-toluensulfinate dihydrate (4.2 g, 18 mmol), chloroacetone (1.0 mL, 12 mmol), n-tetrabutylammonium bromide (0.30 g) and water-benzene-acetone 4:3:3 (10 mL). Work-up and chromatography on silica of the crude using ethyl acetate/n-heptane (1:3 through 1:2) as eluent gave 2.4 g (95%) of the title product as an oil which crystallised on standing in the fridge.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07427631B2uspto-grants-2008_09