Formic Acid → 4,6-Dimethoxy-2-methyl-2H-pyran-3(6H)-one

HRID 46444Notes

Reaction equation

HRID 46444 reaction equation
O[CH:2]([C:4]1([O:13]C)[C:8]([O:9][CH3:10])=[CH:7][CH:6]([O:11][CH3:12])[O:5]1)[CH3:3].C(O)=O.O>CO>[CH3:10][O:9][C:8]1[C:4](=[O:13])[CH:2]([CH3:3])[O:5][CH:6]([O:11][CH3:12])[CH:7]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 962WaterHCID 20348360HCID 20348360, compound

Product 1

HCID 203483594,6-Dimethoxy-2-methyl-2H-pyran-3(6H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2(1-hydroxy ethyl)-2,3,5-trimethoxy-2,5-dihydrofuran (8.4 g, 0.45 moles) in 3 ml methanol was added to 25 ml of formic acid and 1.2 ml methanol. After stirring for 5 minutes, the reaction was poured into 75 ml of water and extracted with chloroform. Concentration of the chloroform layer yielded a brown oil which solidified overnight. Recrystallization from hexane-ether yielded 4,6-dimethoxy-2-methyl-2H-pyran-3(6H)-one as white needles, mp 73°-74.5° C., NMR (CDCl3, δ) 5.75 (1H, d, J=4Hz), 5.3 (1H, d, J=4Hz), 4.62 (1H, q, J=7Hz), 3.68 (3H, s), 3.52 (3H, S), 1.2 (3H, t, J=7Hz).

Workup

  1. extractionextracted with chloroform
  2. customConcentration of the chloroform layer yielded a brown oil which
  3. waitsolidified overnight
  4. customRecrystallization from hexane-ether

Sources & evidence

ORD record
ord-6030428f428448bcb00471d9e833d565
Source dataset
uspto-grants-1979_11
Patent number
US04173572

Reaction notes

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