Dopac → 3,4-Diethoxyphenylacetic acid

HRID 1007372

Reaction equation

HRID 1007372 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].S([O-])(O)(=O)=O.[K+].[C:30](OCC)(=O)[CH3:31].[CH2:36](OS(OCC)(=O)=O)[CH3:37]>O>[CH2:30]([O:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[O:8][CH2:36][CH3:37])[CH3:31]

Participants

7

Reactant 5

HCID 547DopacHCID 6163Diethyl SulfateHCID 8857Ethyl AcetateHCID 516920Potassium bisulfateHCID 17749109Barium hydroxide, octahydrate

Product 1

HCID 5798133,4-Diethoxyphenylacetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

0.8 g of 3,4-dihydroxy-phenylacetic acid and 6.9 g of barium hydroxide octahydrate are dissolved in 50 ml of water and at ambient temperature 2.9 ml of diethylsulphate are added dropwise. The solution is stirred for 2 hours at ambient temperature and for 2 hours at 40° C. After this time the solution is acidified with saturated potassium hydrogen sulphate solution, mixed with ethyl acetate and the suspension is filtered through Celite. The phases are separated and the ethyl acetate phase is dried over sodium sulphate and concentrated by evaporation. The residue obtained is purified through a silica gel column with toluene/ethyl acetate/ethanol (4:2:1) as eluant.

Workup

  1. additionare added dropwise
  2. filtrationthe suspension is filtered through Celite
  3. customThe phases are separated
  4. dry with materialthe ethyl acetate phase is dried over sodium sulphate
  5. concentrationconcentrated by evaporation
  6. customThe residue obtained
  7. customis purified through a silica gel column with toluene/ethyl acetate/ethanol (4:2:1) as eluant

Sources & evidence

ORD record
ord-4b67fc642c024da69356a00d8d3e23ff
Source dataset
uspto-grants-2004_09
Patent number
US06794395B1

Linked notes

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