Acetone → 2-Hydroxy-2-methyl-5-phenylpentane

Participants

Reaction Steps

A mixture of 8.8 g. (0.37 mol.) of magnesium turnings and 150 ml of dry ether was placed in a 3-necked flask fitted with a nitrogen inlet, a reflux condenser and an addition funnel containing 73.7 g (0.37 mol) of 1-bromo-3-phenylpropane. A small amount of the bromo compound was added to the reaction mixture and the mixture warmed in order to initiate reaction. The reaction mixture was treated with 150 ml of dry ether and then the bromo compound was added at such a rate as to maintain gentle reflux. The reaction mixture was heated at reflux for a further 15 minutes and then treated slowly with 21.5 g (0.37 mol) of acetone. The mixture was heated at reflux for a further 30 minutes, cooled and then poured slowly into 300 g of crushed ice. The resultant white precipitate was dissolved by the addition of 20% H2SO4. The organic layer was separated and the aqueous layer extracted with ether. The organic extracts were combined and washed with water and saturated NaCl solution and then dried (MgSO4). The solution was filtered and the solvent removed in-vacuo. The residue was distilled (120° C.; 6 mm) to give the captioned compound as a colorless oil. PMR (CDCl3): δ 1.18 (6H, s), 1.44-1.53 (2 H, m), 1.62-1.72 (2H, m), 2.61 (2H, t, J~7.6 Hz), 7.16-7.30 (5H, m).

Provenance & Evidence