Sodium Hydroxide → 5-Phenylfuran-2-carboxylic acid

HRID 1444203Notes

Reaction equation

HRID 1444203 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[O:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][CH:11]=1)=[O:6]>O.CO>[C:12]1([C:9]2[O:8][C:7]([C:5]([OH:6])=[O:4])=[CH:11][CH:10]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11275689Methyl 5-phenylfuran-2-carboxylate

Product 1

HCID 7362555-Phenylfuran-2-carboxylic acidYield 97.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (200 mg) in water (5 ml) was added to a stirred solution of 5-phenyl-furan-2-carboxylic acid methyl ester (7) (384 mg, 1.90 mmoles) in methanol (20 ml) and the mixture was stirred at room temperature for 4 hours. The solvent was evaporated and the residue was diluted with water (10 ml) and acidified to pH=2 with 1 M aqueous hydrochloric acid. The precipitate was collected, washed with water and the residue was triturated with cyclohexane to afford (8) (350 mg) as a white solid. LC/MS System A; Rt=3.89 mins.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with water (10 ml)
  3. customThe precipitate was collected
  4. washwashed with water
  5. customthe residue was triturated with cyclohexane

Sources & evidence

ORD record
ord-eb9ea6368dcc41dd96d31788d0675df0
Source dataset
uspto-grants-2010_02
Patent number
US07662839B2

Reaction notes

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