4-Hydroxybenzyl Alcohol → (4-{[(2E)-2-(methoxyimino)-2-phenylethyl]oxy}phenyl)methanol
Reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[C:10]([O-:13])([O-])=O.[K+].[K+].[C:16](#[N:18])[CH3:17]>>[CH3:10][O:13]/[N:18]=[C:16](/[C:2]1[CH:9]=[CH:8][CH:5]=[CH:4][CH:3]=1)\[CH2:17][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1Participants
4
Conditions
- Temperature
- 80 °C
Procedure
To a 100 mL RB flask fitted with magnetic stirrer was charged 20 mL of acetonitrile. To the stirred solvent was added 4-Hydroxy-benzylalcohol (0.27 g, 2.175 mmol) and K2CO3 (0.4 g, 2.89 mmol). Then it was stirred for 5 min. 2-Bromo-1-phenyl-ethanone o-methyl-oxime (0.5 g, 2 mmol) was added. Then RM heated 80° C. for 5 h. After completion of the reaction (reaction monitored by TLC), the RM was concentrated in vacuum to remove the acetonitrile. To the residue was then added 10 mL of water and extracted with ethyl acetate (15 mL×2). The organic layer was washed with saturated brine solution (15 mL), dried over anhydrous Na2SO4 and evaporated to dryness gave the titled compound (0.5 g, yield: 92.2%); 1H NMR (300 MHz, DMSO-d6): δ 7.61-7.64 (m, 2H), 7.38-7.40 (t, 3H), 7.18-7.21 (d, 2H), 6.83-6.86 (d, 2H), 5.20 (s, 2H), 5.02-5.06 (t, 1H), 4.38-4.39 (d, 2H), 3.99 (s, 3H).