Sodium Hydroxide → 5-Benzoylfuran-2-carboxylic acid

HRID 659096

Reaction equation

HRID 659096 reaction equation
C[O:2][C:3]([C:5]1[O:6][C:7]([C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:9]=1)=[O:4].[OH-].[Na+]>CO>[C:10]([C:7]1[O:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][CH:8]=1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 107757905-Benzoyl-furan-2-carboxylic acid methyl ester

Product 1

HCID 28772555-Benzoylfuran-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude ester (8) (80 mg, 0.35 mmol) was hydrolysed using Method C, except that MeOH (0.8 mL) and 1 M NaOH (0.8 mL) were used. After the reaction, the solvent was removed under a stream of nitrogen gas, acidified using 1N HCl, extracted with EtOAc, dried (MgSO4), filtered and the solvent concentrated in vacuo to give the crude title compound. Yield: 48 mg; HPLC Purity: >66%; LC tr 0.09 min

Workup

  1. customAfter the reaction
  2. customthe solvent was removed under a stream of nitrogen gas
  3. extractionextracted with EtOAc
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationthe solvent concentrated in vacuo

Sources & evidence

ORD record
ord-24296fc598344a6baed41b0f03dc3459
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Linked notes

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