Acetyl chloride → alpha-Acetoxy-3,4,5-trimethoxyphenyl-acetic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([O:16][CH3:17])[C:13]=1[O:14][CH3:15])[CH:6]([OH:10])[C:7]([OH:9])=[O:8].[C:18](Cl)(=[O:20])[CH3:19]>>[C:18]([O:10][CH:6]([C:5]1[CH:11]=[C:12]([O:16][CH3:17])[C:13]([O:14][CH3:15])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:7]([OH:9])=[O:8])(=[O:20])[CH3:19]Participants
3
Procedure
3,4,5-Trimethoxymandelic acid (80.5 g) was treated with acetyl chloride (150 ml) at room temperature for three hours. The clear solution was concentrated to dryness under vacuum, and the oily residue was crystallized from toluene (280 ml) giving pure α-acetoxy-3,4,5-trimethoxyphenylacetic acid (80.9 g), m.p. 135-139° C.
Workup
- concentrationThe clear solution was concentrated to dryness under vacuum
- customthe oily residue was crystallized from toluene (280 ml)
Sources & evidence
- ORD record