ChemicalBook CAS DataBase List METHYLSULFONYLACETONE

METHYLSULFONYLACETONE synthesis

5synthesis methods

Product Name:METHYLSULFONYLACETONE
CAS Number:5000-46-4
Molecular formula:C4H8O3S
Molecular Weight:136.17

124-63-0
6 suppliers
$10.00/5g

78-95-5
4 suppliers
$16.30/5 g

5000-46-4
69 suppliers
$11.00/1g

Yield:-

Reaction Conditions:

Stage #1:methanesulfonyl chloride with sodium hydrogencarbonate;sodium sulfite in water;acetonitrile at 20;
Stage #2:chloroacetone with potassium iodide in water;acetonitrile at 20;

Steps:

α-Diazo-β-ketosulfones 1; General Procedure 1 (GP1)
General procedure: To a stirred solution of Na₂SO₃ (1.51 g, 12 mmol) and NaHCO₃ (2.02 g, 2.4 mmol) in H₂O (20 mL) was added a solution of the corresponding sulfonyl chloride (10 mmol) in MeCN (5-10 mL) and the mixture was stirred at r.t. for 12-16 h. To the resulting solution were added the corresponding α-haloketone (11 mmol) and KI (83 mg, 0.5 mmol) and the mixture was stirred for 16-20 h. ‘SAFE’ cocktail [prepared by the addition of 3-(chlorosulfonyl)benzoic acid (2.76 g, 12.5 mmol) to a solution of NaN₃ (1.0 g, 15 mmol) and K₂CO₃ (2.1 g, 15.0 mmol) in H₂O (20 mL) and stirring for 10 min] was added to the reaction mixture and stirring was continued for 6 h. If a solid precipitate was formed, the mixture was cooled to 5 °C, the product was filtered, washed with H2O (30 mL) and cold H₂O/EtOH mixture (1:1, 25 mL), and dried in air. Oily precipitates were extracted with DCM (3 × 25 mL), the combined organic phases were dried (CaCl₂), and evaporated to dryness. Additional purification was used, if needed, by flash column chromatography on silica gel or by recrystallization (as indicated).

References:

Dar'In, Dmitry;Kantin, Grigory;Bakulina, Olga;Krasavin, Mikhail [Synthesis (Germany),2020,vol. 52,# 15,p. 2259 - 2266]