Water → 4-Hydroxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester

HRID 29479Notes

Reaction equation

HRID 29479 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[C:10]=1[C:16](=O)[CH3:17])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:1]([O:5][C:6]([C:7]1[O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[C:10]=2[C:16]=1[CH3:17])=[O:19])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 68714827(2-Acetyl-3-hydroxy-phenoxy)-acetic acid tert-butyl ester

Product 1

HCID 138494564-Hydroxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The (2-acetyl-3-hydroxy-phenoxy)-acetic acid tert-butyl ester was dissolved in DMF, and heated to 110-130° C. in the presence of potassium carbonate for 4 hours. The resulting suspension was slowly poured into cold water. The product precipitated out and was collected by filtration. Recrystalyzation in toluene afforded 34.26 g of the desired 4-hydroxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester as pale yellow solid (60% overall yield).

Workup

  1. customThe product precipitated out
  2. filtrationwas collected by filtration
  3. customRecrystalyzation in toluene afforded

Sources & evidence

ORD record
ord-2dd903c2e3414dbd8678fc213c8e2039
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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