Potassium Carbonate → Methyl 6-hydroxy-2-methylbenzofuran-3-carboxylate

HRID 985302Notes

Reaction equation

HRID 985302 reaction equation
C([O:4][C:5]1[CH:14]=[CH:13][C:8]2[CH:9]=[C:10]([CH3:12])[O:11][C:7]=2[CH:6]=1)(=O)C.[C:15](Cl)(=[O:19])C(Cl)=O.[Al+3].[Cl-].[Cl-].[Cl-].[C:25]([O-])([O-])=[O:26].[K+].[K+]>CO>[OH:4][C:5]1[CH:14]=[CH:13][C:8]2[C:9]([C:25]([O:19][CH3:15])=[O:26])=[C:10]([CH3:12])[O:11][C:7]=2[CH:6]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 221435562-Methylbenzofuran-6-yl acetate

Product 1

HCID 22143518Methyl 6-hydroxy-2-methylbenzofuran-3-carboxylateYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This material was prepared from 6-acetoxy-2-methylbenzofuran 89b (0.81 g, 4.3 mmole) by acylation with oxalyl chloride in the presence of AlCl3, followed by treatment with methanol and K2CO3 in a manner as previously described for example 11a to give a beige solid (607 mg, 69%). 1H NMR (DMSO-d6) δ9.64 (1H, s), 7.62 (1H, d, J=8.5 Hz), 6.93 (1H, d, J=1.9 Hz), 6.78 (1H, dd, J=8.5, 2.0 Hz), 3.79 (3H, s), 2.66 (3H, s).

Sources & evidence

ORD record
ord-b7d74162077f4feb88dd46ed041abf6c
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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