Potassium Carbonate → Methyl 4-hydroxy-2-methyl-1-benzofuran-6-carboxylate

HRID 2233360Notes

Reaction equation

HRID 2233360 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[C:7]([O:15]C(=O)C)[C:5]=2[CH:6]=1.C(=O)([O-])[O-].[K+].[K+]>CO.O>[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[C:7]([OH:15])[C:5]=2[CH:6]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 53249530Methyl 4-(acetyloxy)-2-methyl-1-benzofuran-6-carboxylate

Product 1

HCID 46941595Methyl 4-hydroxy-2-methyl-1-benzofuran-6-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-Methyl-4-acetoxy-6-methoxycarbonylbenzofuran (Method 14; 1.275 g, 5.14 mmol) was added to a suspension of potassium carbonate (1.408 g, 10.3 mmol, 2 eq) in MeOH (100 ml) and water (2 ml), and the mixture stirred for 1 hr at ambient temperature. The supernatant liquor was decanted from the insoluble material and evaporated in vacuo to yield a cream solid (2.19 g, assumed to be contaminated with inorganics). NMR: 2.35 (s, 3H), 3.56 (br s, 1H), 3.73 (s, 3H), 6.46 (s, 1H), 6.69 (s, 1H), 6.86 (s, 1H); m/z 205 (M−H)−, 83% by LC-MS.

Workup

  1. customThe supernatant liquor was decanted from the insoluble material
  2. customevaporated in vacuo
  3. customto yield a cream solid (2.19 g, assumed to be contaminated with inorganics)

Sources & evidence

ORD record
ord-aada9727e2de4f1389e0a0564ccf6917
Source dataset
uspto-grants-2010_05
Patent number
US07709505B2

Reaction notes

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