Sodium Hydroxide → 2,6-Di-sec-butylphenol

Participants

Reaction Steps

R-(+)-1-Phenyl-ethyl)-carbamic acid (−) 2,6-di-sec-butylphenyl ester (1b) (4.1 g, 11.6 mmol) was dissolved in a 100 ml 1:1 mixture of dioxane: 1M NaOH aq. The reaction mixture was stirred at 70° C. for 15 min. Volatiles were removed at reduced pressure to a volume of ˜50-70 ml. The pH was adjusted to 3-4 with 1M HCl. The phenol was extracted with ether (3×50 ml), washed with 1 M HCl, brine and dried over anhydrous MgSO4. Evaporation yielded crude yellow oil (2.4 g, ˜100%). Vacuum distillation was performed (120-125° C./˜5 mm) (2.1 g, 89%). Optical rotation: α20D=−14.11° (c=2, pentane).

Provenance & Evidence