Sodium Hydroxide → Maltol

HRID 1461539Notes

Reaction equation

HRID 1461539 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-62bcc4e24c6b42929177040c48ed8fd6
Source dataset
uspto-grants-1991_12
Patent number
US05075461

Reaction notes

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