Phenol → Oxalic acid, diphenyl ester

HRID 703247Notes

Reaction equation

HRID 703247 reaction equation
C(N[C:5]([C:7](NC(=O)C)=[O:8])=[O:6])(=O)C.[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:20][O-:21].[Na+]>C(OCC)C>[C:20]1([O:21][C:5](=[O:6])[C:7]([O:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:8])[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 3016168N,N'-Diacetyloxamide2×HCID 10942334Sodium Methoxide

Product 1

HCID 18475Oxalic acid, diphenyl esterYield 502.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

N,N'-diacetyloxamide (10 g, 0.058 mol), phenol (27.91 g, 0.297 mol) and sodium methoxide (0.2 g, 3.7 mmol) are charged into a three-necked flask equipped with a reflux condenser, a thermometer, an inlet tube for nitrogen, and a magnetic stirrer. The temperature is brought to 130° C., and after two hours the complete disappearance of the N,N'-diacetyloxamide is observed. The reaction mixture is then cooled and ethyl ether (30 ml) is added thereto. The compound of the title is separated from the reaction mixture by crystallization, recovered by filtration and recrystallized from absolute ethyl alcohol, yielding 4.5 g (18.6 mmol) of oxalic acid diphenyl ester with m.p. 132°-5° C.

Workup

  1. customequipped with a reflux condenser
  2. customis brought to 130° C.
  3. temperatureThe reaction mixture is then cooled
  4. customThe compound of the title is separated from the reaction mixture by crystallization
  5. filtrationrecovered by filtration
  6. customrecrystallized from absolute ethyl alcohol

Sources & evidence

ORD record
ord-8ed2785cf2a44ea58b4351da9a105cf9
Source dataset
uspto-grants-1991_01
Patent number
US04981963

Reaction notes

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