Dichloromethane → HCID 86758194, compound

Participants

Reaction Steps

A solution of 4′-methylacetophenone (10 g, 74.5 mmol) and dichloromethane (200 mL) was treated dropwise with boron trifluoroetherate (12.5 mL, 104 mmol) at room temperature. To the resulting solution was added 1,3-propanedithiol (7.45 mL, 74.5 mmol) and the reaction mixture was stirred for 4 h at room temperature. The reaction was quenched carefully with saturated NaHCO3 solution and extracted with dichloromethane. The organic layer was separated and evaporated in vacuo. The residue was dissolved in ethyl acetate and washed with 1 N NaOH, water, and saturated NaCl solution. The organic layer was separated, dried with MgSO4, filtered and solvent evaporated in vacuo to yield a crude oil. Purification of the crude oil via flash chromatography (50% CH2Cl2/hexane) afforded crystalline 4′-methylacetophenone propylene thioketal.

Provenance & Evidence