Sodium Hydroxide → Maltol

HRID 1164275Notes

Reaction equation

HRID 1164275 reaction equation
CO[CH:3]1[O:8][CH:7]([CH3:9])[C:6](=[O:10])[CH:5]=[CH:4]1.ClCl.[OH-:13].[Na+]>C(O)(=O)C.O>[CH3:9][C:7]1[O:8][CH:3]=[CH:4][C:5](=[O:13])[C:6]=1[OH:10]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24526ChlorineHCID 130117926-Methoxy-2-methyl-2H-pyran-3(6H)-one

Product 1

HCID 8369Maltol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 6-methoxy-2-methyl-2H-pyran-3(6H)-one (0.01 mole) in 20 ml of acetic acid was treated with gaseous chlorine (0.01 mole) at room temperature. The reaction mixture was then heated to reflux for about one hour, cooled to room temperature, diluted with 20 ml of water, the pH adjusted with 50% NaOH solution to 7.0 and the reaction mixture extracted with chloroform. The chloroform extract was concentrated to yield maltol which was recrystallized from methanol to give the pure product (56%), mp 159.5°-160.5° C.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for about one hour
  3. extractionthe reaction mixture extracted with chloroform
  4. extractionThe chloroform extract
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-7caa859faa7f4fd1891ee6d3ff71ed52
Source dataset
uspto-grants-1983_01
Patent number
US04368331

Reaction notes

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