Oxalic Acid → 4-Methylcatechol-(p-cresol)

HRID 342821Notes

Reaction equation

HRID 342821 reaction equation
OC[C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5](CO)[C:4]=1[OH:12].C(O)(=O)C(O)=O.[CH3:19][C:20]1[CH:21]=[C:22]([OH:27])[C:23](=[CH:25][CH:26]=1)[OH:24]>O>[CH:3]1[C:4]([OH:12])=[CH:5][CH:6]=[C:7]([CH3:9])[CH:8]=1.[CH3:19][C:20]1[CH:21]=[C:22]([OH:27])[C:23](=[CH:25][CH:26]=1)[OH:24]

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 70392,6-Dimethylol-p-cresolHCID 99584-Methylcatechol

Product 1

HCID 198843874-Methylcatechol-(p-cresol)

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 135 g (0.80 mole) of 2,6-bis(hydroxymethyl)-4-methylphenol, followed by 9 g (0.10 moles) of oxalic acid and 200 g (1.61 moles) of 4-methylcatechol. To this mixture 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-ae76e3e01b854d94a2895ce12c1f2afb
Source dataset
uspto-grants-1999_01
Patent number
US05859153

Reaction notes

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