Acetyl chloride → 1-(3-Tert-butyl-4-hydroxyphenyl)ethanone

Participants

Reaction Conditions

Reaction Steps

To a dry, round bottom flask was added aluminum chloride (4.402 g, 33.0 mmol). The flask was then cooled to −45° C. After 10 minutes, dry toluene (80 mL) was added followed by dropwise addition of 2-tert-butylphenol (5.00 mL, 32.7 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA). The mixture was stirred and maintained at −4° C. After 1.5 hours, acetyl chloride (2.40 mL, 33.8 mmol) was carefully added dropwise. The mixture was allowed to warm to room temperature and monitored with TLC and LC-MS. After 18 hours, the mixture was slowly poured onto crushed ice. This mixture was stirred at room temperature and the crystals were collected by filtration. The light yellow solid was identified as T17.1 (4.2589 g, 68%). MS ESI (pos.) m/e: 193.1 (M+H)+.

Provenance & Evidence