Methanol → (4-Methoxyphenyl)glyoxylic acid

HRID 1859306Notes

Reaction equation

HRID 1859306 reaction equation
C([O:3][C:4](=[O:15])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:6])C.CO>[OH-].[Na+]>[CH3:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([C:5](=[O:6])[C:4]([OH:15])=[O:3])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 2758864Ethyl 2-(4-methoxyphenyl)-2-oxoacetate

Product 1

HCID 584714(4-Methoxyphenyl)glyoxylic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

4-Methoxyphenylglyoxylic ethyl ester obtained in Example 20 was dissolved in 20% sodium hydroxide (60 mg) and methanol (600 ml) and then stirred for 3 hours with heating at 80° C. When the reaction is completed, the reaction solution was extracted with diethyl ether (200 mg) and the obtained aqueous solution was acidified (pH 1-2) with hydrochloric acid. The resulting aqueous acidic solution was extracted with dichloromethane, and the extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to remove the organic solvent to obtain 34.63 g (yield in two reaction steps: 43%) of the title compound as a pale violet solid.

Workup

  1. extractionthe reaction solution was extracted with diethyl ether (200 mg)
  2. extractionThe resulting aqueous acidic solution was extracted with dichloromethane
  3. dry with materialthe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto remove the organic solvent
  6. customto obtain

Sources & evidence

ORD record
ord-1ed1c0550bdc4d9db12c472062f711f3
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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