Benzyl Bromide → 3-Benzyloxy-2-methyl-4-pyrone

HRID 1196221Notes

Reaction equation

HRID 1196221 reaction equation
[Na].[CH3:2][C:3]1[O:9][CH:8]=[CH:7][C:5](=[O:6])[C:4]=1[OH:10].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CO.O>[CH3:2][C:3]1[O:9][CH:8]=[CH:7][C:5](=[O:6])[C:4]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 8369MaltolHCID 5360545Sodium

Product 1

HCID 14901193-Benzyloxy-2-methyl-4-pyrone

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

11.5 g of sodium were dissolved in 300 ml CH3OH and 63g of maltol were added and stirred at room temperature for one hour. 200 ml CH3OH were added and then 102 g benzylbromide were dropped in (30 minutes). Refluxing for 3 hours and distilling off the CH3OH then yielded a residue which was dissolved in 300 ml H2O/300 ml ethyl acetate. The organic phase was washed with water and evaporated. The remaining oil was distilled in vacuo. B.P. (43 mm) =148°-150° C., 81.5 g colorless oil of the title compound was isolated.

Workup

  1. temperatureRefluxing for 3 hours
  2. distillationdistilling off the CH3OH
  3. customthen yielded a residue which
  4. washThe organic phase was washed with water
  5. customevaporated
  6. distillationThe remaining oil was distilled in vacuo

Sources & evidence

ORD record
ord-654808d8a1fc427badab12f9cc9a68c2
Source dataset
uspto-grants-1992_05
Patent number
US05112968

Reaction notes

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