3-Hydroxybenzyl alcohol → 2-[3-(Hydroxymethyl)phenoxy]acetamide

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].Br[CH2:11][C:12]([NH2:14])=[O:13].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:6][CH2:5][C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][CH:7]=1)[O:1][CH2:11][C:12]([NH2:14])=[O:13]

Participants

Procedure

To a solution of 3-hydroxybenzyl alcohol (500 mg, 4 mmol) in acetonitrile (10 mL) was added 2-bromoacetamide (1 eq) and potassium carbonate (1 eq). The resulting suspension was stirred at rt for 18 h. The solvent was removed in vacuo and the residue partitioned between EtOAc and H2O. The aqueous layer was acidified with dilute HCl (2M) and then re-extracted with EtOAc (3×50 mL). The organic phases were combined, dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was purified by column chromatography (EtOAc: methanol) to give 2-(3-(hydroxymethyl)phenoxy)acetamide (320 mg, 43%).