Acetone → 4-(4-Bromophenyl)-4-(hydroxymethyl)cyclohexanone

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask containing (8-(4-bromophenyl)-1,4-dioxaspiro[4.5]decan-8-yl)methanol (4.88 g, 14.91 mmol) was added acetone (34 ml) and water (17 ml) at room temperature. p-toluenesulfonic acid (57 mg, 0.30 mmol) was then added and the mixture heated to 75° C. for 1 hour. The content was cooled to room temperature and concentrated under reduced pressure to remove the excess acetone. The resulting aqueous mixture was extracted with EtOAc twice. The combined organic portion was dried over sodium sulfate and concentrated to afford the title compound as white solid. (4.22 g) LC/MS, ESI-MS: non-ionizable, RT: 1.05 (Condition E).

Provenance & Evidence