Acetophenone → 1-Phenylethanol

Participants

Reaction Steps

Following the set-up of Example 5 and under a nitrogen atmosphere, acetophenone (2.9 g, 3.0 mL, 25 mmol) was added to a solution of B-chlorodiiso-2-ethylapopinocampheylborane (9.6 g, 27.5 mmol) in EE (ethyl ether, 20 mL) at -25° C. The reaction was complete in 48 h (followed by 11B NMR after methanolysis of an aliquot). The reaction was worked up following the procedure of Example 3 to obtain 2.2 g, 72% of α-phenethyl alcohol which was found to be of ≥99% ee by capillary GC analysis of its MTPA ester.

Provenance & Evidence