Citric Acid → Vanillylmandelic Acid

HRID 1492319

Reaction equation

HRID 1492319 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

Reactant 4

HCID 311Citric AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21877243DCM MeOH AcOH

Product 1

HCID 1245Vanillylmandelic Acid

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.

Workup

  1. customVolatiles were removed in vacuo
  2. filtrationinorganics filtered
  3. customto leave a clear yellow solution
  4. customto give the product as one major band Rf 0.10, which
  5. washwas eluted with methanol
  6. customstored at -20° C. in the dark

Sources & evidence

ORD record
ord-cd661af581ed4636935d6e14ccc61d15
Source dataset
uspto-grants-1994_12
Patent number
US05373092

Linked notes

Loading…