Chloroacetone → 1-[(4-Chlorophenyl)sulfanyl]propan-2-one

A stirred solution of 4-chlorothiophenol (47.1 g, 0.326 mole) in sodium hydroxide solution (14.3 g, 0.358 mole in 750 ml water) was treated dropwise over 20 minutes with freshly distilled chloroacetone (28.5 ml, 0.358 mole) and the resulting mixture was stirred for a further 30 minutes at room temperature. The mixture was extracted with ether (3×200 ml) and the organic solution then washed with 2% sodium hydroxide solution (2×200 ml) and water (2×200 ml), dried (MgSO4) and evaporated to dryness to give a quantitative yield of the title compound as a pale yellow solid. A small sample was recrystallized from pentane to yield a colourless crystalline solid m.p. 37°-38° C.

1. extractionThe mixture was extracted with ether (3×200 ml)
2. washthe organic solution then washed with 2% sodium hydroxide solution (2×200 ml) and water (2×200 ml)
3. dry with materialdried (MgSO4)
4. customevaporated to dryness

ORD record

ord-6ace57c7178f4394af4312de67e32342

Source dataset

uspto-grants-1985_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04548948