Sodium Hydroxide → Maltol

HRID 1461542Notes

Reaction equation

HRID 1461542 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-b6a09a79988c469dbc685ebf22b122d9
Source dataset
uspto-grants-1991_12
Patent number
US05075461

Reaction notes

Loading…