ChemicalBook CAS DataBase List Prop-1-ene-1,3-sultone

Prop-1-ene-1,3-sultone synthesis

7synthesis methods

Product Name:Prop-1-ene-1,3-sultone
CAS Number:21806-61-1
Molecular formula:C3H4O3S
Molecular Weight:120.13

A method for producing a Prop-1-ene-1,3-sultone comprises: a step 1 of chlorinating POCl3 or PCl5 with a compound of the chemical formula 2 to produce a compound of the chemical formula 3; a step 2 of diluting the compound of the chemical formula 3 and bromodan (1,3-Dibromo-5,6-dimethylhydantoin) in dichloroethylene solvent and stirring at 20-30°C for four to eight hours to produce 2-halo-1,3-propan sultone of the chemical formula 4; and a step 3 of adding base in the 2-halo-1,3-propan sultone of the chemical formula 4 and stirring for four to eight hours to produce Prop-1-ene-1,3-sultone.

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Yield:21806-61-1 94%

Reaction Conditions:

with methanesulfonyl chloride;triethylamine in ethyl acetate at -20 - 10; for 4 h;Cooling with ice;

Steps:

4

Example 4Synthesis of 1,3-propenesultone (the third step, Reaction Scheme [V]) 2-Hydroxy-1,3-propanesultone (1.70 g, 12.3 mmol) obtained according toExample 3 was dissolved in ethyl acetate (12 mL), and thereafter triethylamine (Et₃N) (2.99 g, 29.5 mmol, produced by Wako Pure Chemical Industries, Ltd.) and methanesulfonyl chloride (MsCl) (1.69 g, 14.7 mmol, produced by Wako Pure Chemical Industries, Ltd.) were added thereto under ice-cooling. The solution was stirred at -20° C. to 10° C. for 4 hours to promote the reaction. After completion of the reaction, water (12 mL) was added to the reaction solution, and then the solution was stirred. Subsequently, the organic layer was separated. After the separated organic layer was washed with water, the organic layer was concentrated, thereafter toluene was added to the concentrated residue. The crystal formed was filtered, and the resultant crystal was dried, to obtain 1,3-propenesultone (1.39 g, yield: 94%) relevant to the above-described general formula [4] as a white crystal. Measurement results of ¹H-NMR are shown below.¹H-NMR (400 MHz, CDCl₃) 6 (ppm): 5.12 (1H), 6.81 (1H), 7.00 (1H).

References:

US2012/130089,2012,A1 Location in patent:Page/Page column 10