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

HRID 1381171Notes

Reaction equation

HRID 1381171 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][O:4][C:3]=1[CH3:9].[OH-].[Na+].[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO>[CH2:12]([O:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][O:4][C:3]=1[CH3:9])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 8369MaltolHCID 14798Sodium Hydroxide

Product 1

HCID 14901193-Benzyloxy-2-methyl-4-pyroneYield 73.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Hydroxy-2-methyl-4-pyrone (22.2 g) in methanol (225 ml) is added to aqueous sodium hydroxide (25 ml H2O containing 7.5 g NaOH). Benzyl chloride (25.5 g) is added and the mixture is refluxed for 6 hours and is then allowed to cool overnight. The bulk of the methanol is removed under vacuum and the residue is treated with water (50 ml). The mixture is extracted into dichloromethane (3×25 ml). The extracts are combined, washed with 5% w/v NaOH (2×25 ml), then water (2×25 ml) and dried over magnesium sulphate. Evaporation of the solvent gives crude 3-benzyloxy-2-methyl-4-pyrone (35 g, 92%) which is purified by distillation in nitrogen under reduced pressure to yield a colourless oil (28 g) of b.p. 148° C./0.2 mm.

Workup

  1. temperaturethe mixture is refluxed for 6 hours
  2. temperatureto cool overnight
  3. customThe bulk of the methanol is removed under vacuum
  4. additionthe residue is treated with water (50 ml)
  5. extractionThe mixture is extracted into dichloromethane (3×25 ml)
  6. washwashed with 5% w/v NaOH (2×25 ml)
  7. dry with materialwater (2×25 ml) and dried over magnesium sulphate
  8. customEvaporation of the solvent
  9. customgives crude 3-benzyloxy-2-methyl-4-pyrone (35 g, 92%) which
  10. distillationis purified by distillation in nitrogen under reduced pressure

Sources & evidence

ORD record
ord-cdd9ca3a54644f02952208bd4b0f8c63
Source dataset
uspto-grants-1986_04
Patent number
US04585780

Reaction notes

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