Catechol → Catechol-(p-methoxyphenol)

HRID 342820

Reaction equation

HRID 342820 reaction equation
C([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5](CO)[C:4]=1[OH:13])O.C(O)(=O)C(O)=O.[C:20]1([C:22](=[CH:24][CH:25]=[CH:26][CH:27]=1)[OH:23])[OH:21]>O>[CH3:10][O:9][C:7]1[CH:8]=[CH:3][C:4]([OH:13])=[CH:5][CH:6]=1.[C:20]1([C:22](=[CH:24][CH:25]=[CH:26][CH:27]=1)[OH:23])[OH:21]

Participants

5

Reactant 3

HCID 289CatecholHCID 971Oxalic AcidHCID 8274592,6-Bis(hydroxymethyl)-4-methoxyphenol

Product 1

HCID 70292826Catechol-(p-methoxyphenol)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a 1 liter, 3 necked round bottomed flask equipped with a paddle stirrer, condenser, thermometer and heating source, were added 150 g (0.81 mole) of the 2,6-dimethylol-4-methoxyphenol, followed by 9 g (0.1 moles) of oxalic acid and 180 g (1.63 moles) of catechol. To this were added 400 g of water. The reaction mixture was stirred and heated to 70° C. Solution occurred when the temperature reached approximately 60° C. Then, the reaction mixture was heated to reflux and held at reflux for 4 hours. After 1 hour at reflux, the product began to separate.

Workup

  1. customTo a 1 liter, 3 necked round bottomed flask equipped with a paddle stirrer, condenser
  2. temperaturethermometer and heating source
  3. customreached approximately 60° C
  4. temperatureThen, the reaction mixture was heated
  5. temperatureto reflux
  6. temperatureat reflux for 4 hours
  7. temperatureAfter 1 hour at reflux
  8. customto separate

Sources & evidence

ORD record
ord-76b5387c60b046c1a78a9731b9499814
Source dataset
uspto-grants-1999_01
Patent number
US05859153

Linked notes

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