Citric Acid → Vanillylmandelic Acid

반응식

[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]

참가 물질

반응물 4

HCID 311Citric Acid

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 21877243DCM MeOH AcOH

생성물 1

HCID 1245Vanillylmandelic Acid

실험 절차

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.