1-Propanol → 5-Chlorolevulinic acid propyl ester

HRID 1391855Notes

Reaction equation

HRID 1391855 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH2:4][CH2:5][C:6]([CH2:8][Cl:9])=[O:7].[CH2:11](O)[CH2:12]C>S(=O)(=O)(O)O>[CH2:1]([O:2][C:3](=[O:10])[CH2:4][CH2:5][C:6]([CH2:8][Cl:9])=[O:7])[CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 10311-PropanolHCID 11789557Methyl 5-chloro-4-oxopentanoate

Product 1

HCID 865974235-Chlorolevulinic acid propyl ester

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 5-chlorolevulinic acid methyl ester (10 g) in 1-propanol (50 ml) and concentrated sulfuric acid was added (0.5 ml) and the reaction mixture was refluxed for 3 h. Thereafter, the methanol and the excess 1-propanol were distilled in vacuo. Dichloromethane was added to the residue and the organic layer was washed with saturated aqueous sodium hydrogen carbonate and water. Drying of the organic layer with Na2SO4 followed by distillation of the solvent in vacuo yielded 5.4 g (quant.) 5-chlorolevulinic acid propyl ester. The NMR data agreed with the data for the product obtained according to Example 4.

Workup

  1. temperaturethe reaction mixture was refluxed for 3 h
  2. distillationThereafter, the methanol and the excess 1-propanol were distilled in vacuo
  3. additionDichloromethane was added to the residue
  4. washthe organic layer was washed with saturated aqueous sodium hydrogen carbonate and water
  5. dry with materialDrying of the organic layer with Na2SO4
  6. distillationfollowed by distillation of the solvent in vacuo

Sources & evidence

ORD record
ord-d5aa7f1b041947a1a0a3bee03be1ac63
Source dataset
uspto-grants-2008_03
Patent number
US07339073B2

Reaction notes

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