Sodium Acetate → 2-[(Acetyloxy)methyl]4-(2-chloroethoxy)-5-methoxybenzyl acetate
Reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([CH2:11]Cl)[C:8]([CH2:13]Cl)=[CH:7][C:6]=1[O:15][CH3:16].[C:17]([O-:20])(=[O:19])[CH3:18].[Na+]>C(O)(=O)C>[C:17]([O:20][CH2:13][C:8]1[CH:7]=[C:6]([O:15][CH3:16])[C:5]([O:4][CH2:3][CH2:2][Cl:1])=[CH:10][C:9]=1[CH2:11][O:20][C:17](=[O:19])[CH3:18])(=[O:19])[CH3:18]Participants
4
Procedure
To a solution of 5.67 g (20 mmol) of 36 in 75 mL of acetic acid was added a solution of 3.5 g of anhydrous sodium acetate (42.7 mmol) in 100 mL of acetic acid. This mixture was refluxed with stirring for 2 h. Solids were removed by filtration and washed with acetic acid. The filtrate was evaporated to approximately 30 mL, then poured into water and extracted with ether. The organic phase was washed with aqueous sodium carbonate, water, and brine. After drying over sodium sulfate, the solution was filtered and evaporated to give 5.69 g (86%) of 2-[(acetyloxy)methyl]-4-(2-chloroethoxy)-5-methoxybenzyl acetate (37) as a white solid, mp 79-80° C.