Sodium Hydroxide → Maltol

HRID 466292Notes

Reaction equation

HRID 466292 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 40%

Procedure

3-Benzoyloxy-2-methyl-4-pyrone (40.60 g, 176.5 mmol) is stirred at 20°-25° C. for 3 hours with 265 ml (530 mmol) of 2N sodium hydroxide solution. The solution is adjusted to pH 6.5 and extracted three times with 200 ml of dichloromethane each time. The combined organic phases are dried over sodium sulphate and concentrated on a rotary evaporator. The crude product is recrystallized in acetone and gives 8.90 g (40%) of 3-hydroxy-2-methyl-4-pyrone, m.p. 156°-158° C.

Workup

  1. extractionextracted three times with 200 ml of dichloromethane each time
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. concentrationconcentrated on a rotary evaporator
  4. customThe crude product is recrystallized in acetone

Sources & evidence

ORD record
ord-96be7891f610415cbfa6773fa45d019a
Source dataset
uspto-grants-1992_10
Patent number
US05155254

Reaction notes

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