Methanol → Methyl hexyl cyclopentanone carboxylate

HRID 328052Notes

Reaction equation

HRID 328052 reaction equation
[CH2:1]([CH:7]1[C:11](=[O:12])[CH2:10][CH2:9][CH:8]1[C:13]([OH:15])=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH3:16]O.S(=O)(=O)(O)O>C(Cl)CCl>[CH2:1]([CH:7]1[C:11](=[O:12])[CH2:10][CH2:9][CH:8]1[C:13]([O:15][CH3:16])=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 20574896Cyclopentanecarboxylic acid, 2-hexyl-3-oxo-

Product 1

HCID 162249Methyl hexyl cyclopentanone carboxylate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 17 g of 2-n-hexyl-3-oxo-cyclopentanecarboxylic acid, 10 ml of methanol and 1 g of concentrated sulphuric acid in 50 ml of ethylene chloride, is refluxed for 8 hours. The reaction mixture is then washed with water and sodium carbonate solution and dried over anhydrous sodium sulphate. The solvent is distilled off at a reduced pressure and the residue is distilled through a short Vigreux column. The product, methyl 2-n-hexyl-3-oxo-cyclopentanecarboxylate is collected at 85° C/0,06 mm, yield 17 g (93%), nD20 1.4562.

Workup

  1. washThe reaction mixture is then washed with water and sodium carbonate solution
  2. dry with materialdried over anhydrous sodium sulphate
  3. distillationThe solvent is distilled off at a reduced pressure
  4. distillationthe residue is distilled through a short Vigreux column
  5. customThe product, methyl 2-n-hexyl-3-oxo-cyclopentanecarboxylate is collected at 85° C/0,06 mm, yield 17 g (93%)

Sources & evidence

ORD record
ord-dcb42ad37492466590fe593c278035cd
Source dataset
uspto-grants-1977_04
Patent number
US04016109

Reaction notes

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