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

HRID 1492025Notes

Reaction equation

HRID 1492025 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>CO>[O:4]1[CH2:1][CH2:11][CH:7]([C:8]([O:9][CH3:10])=[O:12])[CH2:6][CH2:5]1

Participants

3

Reactant 1

HCID 110083843-[2-(Acetyloxy)ethyl]dihydro-2(3H)-furanone

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution consisting of 57 wt % of 3-(2'-acetoxyethyl)-dihydro-2(3H)furanone and 43wt % of methanol was pumped into an evaporator (300° C.) at a rate of 170 g per hour, whence the vapors were passed together with 80 L/h of nitrogen over 560 g (950 mL) of Al2O3 (1.3 mm extrudates) at a reactor temperature of 250° C. using a trickle-bed method. The gaseous effluent was condensed in cold traps and analyzed by gas chromatography. 61 mol % of methyl tetrahydropyran-4-carboxylate was formed, plus 26 mol % of 3-(2'-methoxyethyl)-dihydro-2(3H)furanone and 5 mol % of 5-oxaspiro[2.4]heptan-4-one. The conversion of 3-(2'-acetoxyethyl)-dihydro-2(3H)furanone was 97%.

Workup

  1. customwas pumped into an evaporator (300° C.) at a rate of 170 g per hour, whence the vapors
  2. customwere passed together with 80 L/h of nitrogen over 560 g (950 mL) of Al2O3 (1.3 mm extrudates) at a reactor
  3. customtemperature of 250° C.
  4. customcondensed in cold traps

Sources & evidence

ORD record
ord-d4db3e89e4f442b1b0460d72cabe9dfe
Source dataset
uspto-grants-1994_12
Patent number
US05371246

Reaction notes

Loading…