Sodium Carbonate → HCID 22915484, compound

Participants

Reaction Steps

To a solution in dichloromethane (20 mL) containing a few drops of DMF of 4-(3-iodophenoxy)butanoic acid (2.26 g, 7.38 mmol) was added oxalyl chloride (0.60 mL, 6.9 mmol) slowly via syringe. The reaction mixture was stirred for 30 minutes at ambient temperature, and then was decanted into a dichloromethane solution of O-benzylhydroxylamine (3.5 g, 22 mmol; prepared by shaking O-benzylhydroxylamine in a mixture of dichloromethane and saturated aqueous Na2CO3, separating the layers, and drying the organic phase over MgSO4). The reaction mixture was stirred for 3.5 hours at ambient temperature and then was extracted with water and saturated aqueous Na2CO3. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give a white solid. The solid was dissolved in dichloromethane and the organic solution was washed with aqueous 1M HCl, dried over MgSO4, filtered, and concentrated in vacuo to give O-benzyl-4-(3-iodophenoxy)butanohydroxamic acid (3.12 g) as a fluffy white solid.

Provenance & Evidence