Sodium Hydroxide → Maltol

HRID 466289Notes

Reaction equation

HRID 466289 reaction equation
C([O:9][C:10]1[C:15](=[O:16])[CH:14]=[CH:13][O:12][C:11]=1[CH3:17])(=O)C1C=CC=CC=1.[OH-].[Na+]>>[OH:9][C:10]1[C:15](=[O:16])[CH:14]=[CH:13][O:12][C:11]=1[CH3:17]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 802553-(Benzoyloxy)-2-methyl-4H-pyran-4-one

Product 1

HCID 8369MaltolYield 69.3%

Procedure

3-Benzoyloxy-2-methyl-4-pyrone (19.00 g, 82.6 mmol) is stirred at 20°-25° C. for 3 hours with 124 ml (248 mmol) of 2N sodium hydroxide solution. The solution is adjusted to pH 6.5 and extracted three times with 100 ml of dichloromethane each time. The combined organic phases are dried over magnesium sulphate and concentrated on a rotary evaporator. The crude product is recrystallized in acetone and gives 7.21 g (69.3%) of 3-hydroxy-2-methyl-4-pyrone, m.p. 157°-158° C.

Workup

  1. extractionextracted three times with 100 ml of dichloromethane each time
  2. dry with materialThe combined organic phases are dried over magnesium sulphate
  3. concentrationconcentrated on a rotary evaporator
  4. customThe crude product is recrystallized in acetone

Sources & evidence

ORD record
ord-617d3f9b0c3644f9804603db602f1057
Source dataset
uspto-grants-1992_10
Patent number
US05155254

Reaction notes

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