Sodium Methoxide → Methyl 6-hydroxy-1,4-benzodioxin-2-carboxylate

HRID 1756032Notes

Reaction equation

HRID 1756032 reaction equation
C[O-].[Na+].C([O:7][C:8]1[CH:22]=[CH:21][C:11]2[O:12][C:13]([C:16]([O:18][CH2:19]C)=[O:17])=[CH:14][O:15][C:10]=2[CH:9]=1)(=O)C>CO>[OH:7][C:8]1[CH:22]=[CH:21][C:11]2[O:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][O:15][C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 11043631HCID 11043631, compound

Product 1

HCID 19392464Methyl 6-hydroxy-1,4-benzodioxin-2-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add 3.8 mmol of a 2M solution of sodium methanolate to a solution of 0.38 mmol of ethyl 6-acetoxy-1,4-benzodioxin-2-carboxylate in 5 cm3 of anhydrous methanol. After stirring for 4 hours at room temperature and neutralising with acid Dowex resin, the reaction mixture is concentrated under reduced pressure and the crude product obtained is purified by chromatography on a silica column (eluant: petroleum ether/diethyl ether, 80:20). Methyl 6-hydroxy-1,4-benzodioxin-2-carboxylate is thereby obtained in a yield of 87%.

Workup

  1. concentrationthe reaction mixture is concentrated under reduced pressure
  2. customthe crude product obtained
  3. customis purified by chromatography on a silica column (eluant: petroleum ether/diethyl ether, 80:20)

Sources & evidence

ORD record
ord-295ece9631ee44eaad2a34b2fe24bbd3
Source dataset
uspto-grants-1995_08
Patent number
US05439909

Reaction notes

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