3-[2-(Acetyloxy)ethyl]dihydro-2(3H)-furanone → 2H-Pyran-4-carboxylic acid, tetrahydro-, methyl ester

HRID 1492029Notes

Reaction equation

HRID 1492029 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH:7]1[CH2:11][CH2:10][O:9][C:8]1=[O:12])(=O)C.COCCC1CCOC1=O>[O-2].[Al+3].[O-2].[O-2].[Al+3].CO>[O:4]1[CH2:1][CH2:11][CH:7]([C:8]([O:9][CH3:10])=[O:12])[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 110083843-[2-(Acetyloxy)ethyl]dihydro-2(3H)-furanoneHCID 14228512Dihydro-3-(2-methoxyethyl)-2(3H)-furanone

Product 1

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

Reagents, catalysts & solvents 2

HCID 9989226AluminaCatalystHCID 887MethanolSolvent

Procedure

A solution consisting of 37 wt % of 3-(2'-acetoxyethyl)-dihydro-2(3H)furanone, 19 wt % of 3-(2'-methoxyethyl)dihydro-2(3H)furanone, and 44 wt % of methanol, was passed over 140 g of aluminum oxide catalyst (1.5 mm extrudates) in a tubular reactor at a rate of 38 g per hour with the addition of 10 Lh of nitrogen, at a temperature of 250° C. The gaseous effluent was condensed in cold traps and analyzed by gas chromatography. 53 mol % of methyl tetrahydropyran-4-carboxylate was formed, plus 41 mol % of 3-(2'-methoxyethyl)-dihydro-2(3H)furanone and 3 mol % of 5-oxaspiro[2.4 ]heptan-2-one. The conversion of 3-(2'-acetoxyethyl)-dihydro-2(3H)furanone was better than 99%.

Workup

  1. customcondensed in cold traps

Sources & evidence

ORD record
ord-bfb93d196c604c9eab1b0031ec64076c
Source dataset
uspto-grants-1994_12
Patent number
US05371246

Reaction notes

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