Hydrochloric Acid → HCID 86652996, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of aluminum chloride (162.3 g, 1.22 mol) in methylene chloride (600 mL) at −75° C. was added acetyl chloride (95.7 g, 1.22 mol) while stirring under an atmosphere of argon. 2-tert-Butyl-phenol (167 g, 1.11 mol) was added dropwise over 1 hr. The resulting mixture was allowed to warm to 0° C. for 10 min. The resulting mixture was then quenched with ice and extracted with EtOAc (1.5 L). The organic layer was separated and dried with brine. The organic layer was evaporated in vacuo to yield a white solid. The white solid was dissolved in methanol (300 mL) and treated with potassium carbonate (100 g) and the resulting mixture allowed to stir 18 h at room temperature. Water (300 mL) was added and pH adjusted to 5 to 6 using concentrated hydrochloric acid. The resulting mixture was extracted with EtOAc. The organic layer was rinsed with brine and dried over sodium sulfate, then evaporated in vacuo to yield 1-(4-tert-butyl-3-hydroxy-phenyl)-ethanone as a tan solid. C12H16O2; MS (ESI) m/z 193.2 (MH)+.

Provenance & Evidence