Methanol → 2H-Pyran-4-carboxylic acid, tetrahydro-, methyl ester

HRID 1492027Notes

Reaction equation

HRID 1492027 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[CH2:8][CH2:7][O:6][C:5]1=[O:9].[CH3:10]O>O>[O:1]1[CH2:2][CH2:3][CH:4]([C:5]([O:6][CH3:10])=[O:9])[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 887MethanolHCID 14047240Dihydro-3-(2-hydroxyethyl)-2(3H)-furanone

Product 1

HCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution consisting of 45 wt % of 3-(2'-hydroxyethyl)-dihydro-2(3H)furanone, 45 wt % of methanol, and 10 wt % of water, was evaporated at a rate of 25 g per hour and the vapors were passed over 90 g of aluminum oxide catalyst (diameter 1.5 ram) in a tubular reactor at a temperature of 250° C. The gaseous effluent was condensed in cold traps and analyzed by gas chromatography. The experiment was carried out for a period of 60 h and the total amount of starting material used was 1500 g. 57 mol % of methyl tetrahydropyran-4-carboxylate was formed, plus 32 mol % of 3-(2'-methoxyethyl)-dihydro-2(3H)furanone and 4 mol % of 5-oxaspiro-[2.4 ]heptan-2-one, the conversion of 3-(2'-hydroxyethyl)-dihydro-2(3H)furanone being better than 97%.

Workup

  1. customwas evaporated at a rate of 25 g per hour
  2. customthe vapors were passed over 90 g of aluminum oxide catalyst (diameter 1.5 ram) in a tubular reactor at a temperature of 250° C
  3. customcondensed in cold traps

Sources & evidence

ORD record
ord-a7f20205c3f6416db3013270c73bf890
Source dataset
uspto-grants-1994_12
Patent number
US05371246

Reaction notes

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