Methanol → 2-methoxy-2-phenyl-4-(4-carboxyphenyl)-3(2H)-furanone

HRID 259443Notes

Reaction equation

HRID 259443 reaction equation
[OH:1][C:2]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][O:3]1.[CH3:23]O>>[CH3:23][O:1][C:2]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:6](=[O:7])[C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([OH:16])=[O:15])=[CH:12][CH:13]=2)=[CH:4][O:3]1

Participants

3

Reactant 2

HCID 887MethanolHCID 203044972-hydroxy-2-phenyl-4-(4-carboxyphenyl)-3(2H)-furanone

Product 1

HCID 202353942-methoxy-2-phenyl-4-(4-carboxyphenyl)-3(2H)-furanoneYield 91.6%

Procedure

A solution of 1.50 g of 2-hydroxy-2-pheny-4-(4-carboxyphenyl)-3(2H)-furanone in 100 ml of methanol was heated under reflux with stirring for 17 hrs. THe reaction mixture was concentrated to a volume of 20 ml, seeded with the product and the precipitate was collected after standing at 0° C. for 3 days. The precipitate was collected, washed with cold methanol and ether and dried at 0° C. for 4 hrs. to give 1.42 g (91.6%) of 2-methoxy-2-phenyl-4-(4-caboxyphenyl)-3(2H)-furanone as colorless crystals, m.p. 212°-214° C.

Workup

  1. temperatureunder reflux
  2. concentrationTHe reaction mixture was concentrated to a volume of 20 ml
  3. customthe precipitate was collected
  4. waitafter standing at 0° C. for 3 days
  5. customThe precipitate was collected
  6. washwashed with cold methanol and ether
  7. customdried at 0° C. for 4 hrs

Sources & evidence

ORD record
ord-2218003ec77b421db06c3c9427307d93
Source dataset
uspto-grants-1977_07
Patent number
US04038289

Reaction notes

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