Acetic Acid → HCID 59128696, compound

Participants

Reaction Steps

A mixture of 25 (1.00 g, 2.20 mmol), glacial acetic acid (5.0 mL), H2O (5.0 mL) and 30% aq. H2O2 (370 μL, 3.30 mmol) were stirred for 8 h and partitioned between AcOEt/brine. The layers were separated, the aqueous phase extracted with more AcOEt and the combined organic extracts dried (MgSO4) and concentrated to give 27 as a creamy white solid (731 mg, 96%); 1H NMR (400 MHz, CDCl3) δ-0.058 (s, 9H), 0.92 (t, J=8.3 Hz, 2H), 3.58 (t, J=8.3 Hz, 2H), 4.01 (s, 3H), 2.01 (s, 2H), 7.37 (s, 1H), 7.56 (s, 1H), 7.66 (d, J=2.3 Hz, 1H), 7.95 (s, 1H), 8.17 (d, J=2.2 Hz, 1H), 9.00-9.60 (bs, OH).

Provenance & Evidence