Citric Acid → Vanillylmandelic Acid
Reaction equation
[OH-:1].[Na+].Cl.[C:4]([OH:16])(=[O:15])[CH2:5][C:6]([CH2:11][C:12]([OH:14])=O)([C:8](O)=O)O.ClCCl.[CH3:20]O.[C:22]([OH:25])(=O)[CH3:23]>>[CH3:20][O:14][C:12]1[CH:11]=[C:6]([CH:5]([OH:1])[C:4]([OH:16])=[O:15])[CH:8]=[CH:23][C:22]=1[OH:25]Participants
5
Procedure
The resulting compound was deprotected, by treatment with 1M sodium hydroxide (500 microliter) for 30 minutes at room temperature in the dark. The reaction mixture was taken to pH 3 with 2M hydrochloric acid (200 microliter) and then 1M citric acid (1.5 ml). Volatiles were removed in vacuo, the residue taken up in methanol, and inorganics filtered to leave a clear yellow solution. This was subjected to TLC (eluent dichloromethane-methanol-acetic acid 75:25:1) to give the product as one major band Rf 0.10, which was eluted with methanol and stored at -20° C. in the dark.