Dihydro-3-(2-methoxyethyl)-2(3H)-furanone → 2H-Pyran-4-carboxylic acid, tetrahydro-, methyl ester

HRID 1492028Notes

Reaction equation

HRID 1492028 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH:5]1[CH2:9][CH2:8][O:7][C:6]1=[O:10]>CO>[O:2]1[CH2:3][CH2:4][CH:5]([C:6]([O:7][CH3:8])=[O:10])[CH2:9][CH2:1]1.[CH2:4]1[C:5]2([CH2:9][CH2:8][O:7][CH2:6]2)[C:3]1=[O:2]

Participants

4

Reactant 1

HCID 14228512Dihydro-3-(2-methoxyethyl)-2(3H)-furanone2×

Product 2

HCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl esterHCID 18954383HCID 18954383, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

During an experimental period of 36 h a total of 900 g of a solution consisting of 53 wt % of 3-(2'-methoxyethyl)-dihydro-2(3H)furanone and 47 wt % of methanol was evaporated and the vapors were passed over 90 g of aluminum oxide catalyst (diameter 1.5 ram) at a temperature of 250° C. in a tubular reactor. Following condensation of the gaseous effluent, analysis was effected using gas chromatography. The conversion of 3-(2'-methoxyethyl)-dihydro-2(3H)furanone was 53%. 46 mol % of methyl tetrahydropyran-4-carboxylate and 7 mol % of 5-oxaspiro-[2.4 ]heptan-2-one were formed.

Workup

  1. customwas evaporated
  2. customthe vapors were passed over 90 g of aluminum oxide catalyst (diameter 1.5 ram) at a temperature of 250° C. in a tubular reactor
  3. customcondensation of the gaseous effluent, analysis

Sources & evidence

ORD record
ord-7e5accfc45fa4e7abd00fc0b78e280fe
Source dataset
uspto-grants-1994_12
Patent number
US05371246

Reaction notes

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