Methanol → 3-Benzyloxy-2-methyl-4-pyrone

HRID 566859Notes

Reaction equation

HRID 566859 reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[CH:5][C:6](=[O:9])[C:7]=1[OH:8].[CH2:10](Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CO.[OH-].[Na+]>O>[CH3:1][C:2]1[O:3][CH:4]=[CH:5][C:6](=[O:9])[C:7]=1[O:8][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7503Benzyl ChlorideHCID 8369MaltolHCID 14798Sodium Hydroxide

Product 1

HCID 14901193-Benzyloxy-2-methyl-4-pyroneYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20.0 g (159 mmol) of 2-methyl-3-hydroxy-4-pyranone and 22.1 g (175 mmol, 1.1 eq.) of benzyl chloride are introduced into 200 mL of methanol; then 6.98 g (175 mmol) of NaOH in 22 mL of water are added. The reaction medium is reflux agitated for 6½ hours. The solvent is subsequently evaporated and the residue retaken up with 100 mL of dichloromethane. This solution is then washed with a 5% aqueous solution of soda (2×80 mL) and with water (2×80 mL). The organic phases are collected, dried on sodium sulphate, filtered and evaporated under reduced pressure; 32.3 g (149 mmol) of 2-methyl-3-benzyloxy-4-pyranone are isolated. Yield: 94%.

Workup

  1. temperatureThe reaction medium is reflux
  2. customThe solvent is subsequently evaporated
  3. washThis solution is then washed with a 5% aqueous solution of soda (2×80 mL) and with water (2×80 mL)
  4. customThe organic phases are collected
  5. customdried on sodium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-928a8176c2b84510a2a5c55818bac13d
Source dataset
uspto-grants-2001_01
Patent number
US06177409B1

Reaction notes

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