Phenol → HCID 5462712, compound

HRID 1599394Notes

Reaction equation

HRID 1599394 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].[C:9]1(=[O:15])[O:14][C:12](=[O:13])[CH:11]=[CH:10]1>C1(C)C=CC=CC=1>[C:1]1([O:7][C:9](=[O:15])/[CH:10]=[CH:11]/[C:12]([OH:14])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 7923Maleic AnhydrideHCID 5360545Sodium

Product 1

HCID 5462712HCID 5462712, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of phenol (22.41 g), sodium (5.47 g) and toluene (500 ml) was heated for 4 hours while refluxing. The reaction mixture was cooled to 85° C., and maleic anhydride (23.35 g) was added. After stirring at 85° C. for 1 hour, the reaction mixture was poured over ice-water, and the aqueous layer was collected. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and then treated with activated charcoal, after which the solvent was distilled off, to yield fumaric acid monophenyl ester (10.59 g, 23%), which was then recrystallized from ethyl acetate-hexane to yield colorless needles having a melting point of 127° to 128° C.

Workup

  1. temperaturewas heated for 4 hours
  2. temperaturewhile refluxing
  3. customthe aqueous layer was collected
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried (MgSO4)
  7. additiontreated with activated charcoal
  8. distillationafter which the solvent was distilled off

Sources & evidence

ORD record
ord-cc9f6682cdfc4f8e8b2b9a5de123cc62
Source dataset
uspto-grants-1998_04
Patent number
US05741784

Reaction notes

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