Isopropanol → HCID 51347808, compound

Participants

Reaction Steps

A mixture of 4-(dimethylammonio)butanoate (4) (7.87 g, 0.06 mol) and ethyl bromide (13.08 g, 0.12 mol) in anhydrous acetone (20 ml) was refluxed until the starting material 4-(dimethylammonio)butanoate disappeared (TLC control, methanol-aquous ammonium hydroxide, 3:1)). The reaction mixture was supplemented with isopropanol (100 ml) and the solution was evaporated to dryness. A solution of solution of KOH (7.28 g, 0.13 mol) in 96% ethanol (70 ml) was added to the residue at 0° C. and reaction mixture was stirred for 4 hours. The precipitate was filtered off and the filtrate was treated with 2 N HCI in methanol until the pH of the medium was 7-8. The reaction mixture was kept at −18° C. for 12 hours and was filtered. The filtrate was evaporated to dryness and the residue was azeotropically dried with isopropanol (3×100 ml). The obtained oily solid (13.4 g) was dissolved in isopropanol (100 ml) and was kept at −18° C. for 12 hours. The precipitate was filtered and the filtrate was evaporated to dryness and crystallized from acetone (30 ml) at −18° C. to give 4.14 g (43%) of 4-[ethyl(dimethyl)ammonio]butanoate.

Provenance & Evidence