Homovanillic Acid → 4-(Acetyloxy)-3-methoxybenzeneacetic acid

HRID 2050555Notes

Reaction equation

HRID 2050555 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]([OH:20])(=[O:19])[CH2:9][C:10]1[CH:18]=[CH:17][C:15]([OH:16])=[C:12]([O:13][CH3:14])[CH:11]=1>O>[C:1]([O:16][C:15]1[CH:17]=[CH:18][C:10]([CH2:9][C:8]([OH:20])=[O:19])=[CH:11][C:12]=1[O:13][CH3:14])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 1738Homovanillic AcidHCID 7918Acetic Anhydride

Product 1

HCID 2264844-(Acetyloxy)-3-methoxybenzeneacetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Specifically, acetic anhydride (120 mL) was added to 30.0 g (165 mmol) homovanillic acid and the mixture was allowed to reflux for 6 hours. The solvent was evaporated, leaving an oil which was poured into 1L H2O and allowed to stir overnight. The solid was collected and dried in vacuo to give 33.1 g of 4-acetoxy-3-methoxyphenylacetic acid.

Workup

  1. temperatureto reflux for 6 hours
  2. customThe solvent was evaporated
  3. customleaving an oil which
  4. customThe solid was collected
  5. customdried in vacuo

Sources & evidence

ORD record
ord-800bff976e9945a5a3cd381857345bac
Source dataset
uspto-grants-1991_05
Patent number
US05013759

Reaction notes

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