Peracetic Acid → 2-(2,3-Epoxypropyl)phenol

Participants

Reaction Steps

2-Allylphenol (10 g, 0.075 mol) was added to a solution of peracetic acid (30 g, 30% active) in dichloromethane (100 ml) that had been dried over anhydrous MgSO4. The reaction mixture was stirred at room temperature for 48 hrs. The dichloromethane solution was washed with water, dilute aqueous NaCO3, dilute aqueous NaSO3 and dried over anhydrous MgSO4. After evaporation of the solvent in vacuo, 2-(2,3-epoxypropyl)phenol was isolated as viscous liquid. MS m/z 150 (M+ calcd for C9H10O2150). H NMR (300 MHz, CDCL3) d 2.65-2.80(m, 2, CH2 epoxypropyl), 2.87-2.93 (m, 1, CH2 epoxypropyl), 3.10-3.21 (m, 1, CH2 epoxypropyl), 3.50-3.60 (m, 1, CH epoxypropyl), 6.80-7.25 (m, 4, aromatic). 2-(2,3-Epoxypropyl)phenol (0.9 g, 0.006 mol) was added to a solution of powdered sodium hydroxide (0.24 g, 0.006 mol) in dimethylacetamide(30 ml) and the solution heated at 80C for 1 hr. The reaction mixture was diluted with water and extracted with dichloromethane, dried over anhydrous MgSO4 and evaporated in vacuo to give a solid that on recrystallization from methanol gave product mp 150-152C. MS m/z 376 (M+ cacld for C22H20N2O4=376). H NMR (300 MHz, CDCl3) d 3.62 (dq, 2, CH2 epoxypropyl), 4.57 (dq, 2, CH2 epoxypropyl), 5.15-5.32 (m, 1, CH epoxypropyl), 6.78-6.93 (m, 2, aromatic), 7.11 (s, 1, heteroaromatic), 7.15-7.28(m, 2, aromatic).

Provenance & Evidence