Ethanol → Ethyl levulinate

HRID 1952852Notes

Reaction equation

HRID 1952852 reaction equation
[O:1]=[C:2]([CH3:8])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH2:9](O)[CH3:10].S(=O)(=O)(O)O.O>C1C=CC=CC=1>[O:1]=[C:2]([CH3:8])[CH2:3][CH2:4][C:5]([O:7][CH2:9][CH3:10])=[O:6]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 11579Levulinic Acid

Product 1

HCID 10883Ethyl levulinate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

100 g (0.86 mol) of 4-oxopentanoic acid, 150 g of ethanol and 1 ml of sulfuric acid in 200 ml of benzene were refluxed until water separation in the Dean-Stark trap ceased. The cooled reaction mixture was washed with water, sodium carbonate solution and again with water and then dried under reflux with the Dean-Stark trap. When removal of the water phase was complete, the solvent was removed by distillation and the residue was distilled under reduced pressure. Boiling point 85-87° C./16 mm Hg, yield 105.5 g (85%).

Workup

  1. customThe cooled reaction mixture
  2. washwas washed with water, sodium carbonate solution and again with water
  3. customdried
  4. temperatureunder reflux with the Dean-Stark trap
  5. customWhen removal of the water phase
  6. customthe solvent was removed by distillation
  7. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-132707b9dc764ce49b45d92d93b157c7
Source dataset
uspto-grants-2000_09
Patent number
US06114358

Reaction notes

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