Sodium Hydroxide → Maltol

HRID 25909

Reaction equation

HRID 25909 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-7f1252b2941e457884750f3b255f5eb4
Source dataset
uspto-grants-1979_04
Patent number
US04147705

Linked notes

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