Methanol → 3-Oxo-cyclopentanecarboxylic acid methyl ester

HRID 1680362Notes

Reaction equation

HRID 1680362 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3]1.S(=O)(=O)(O)O.[CH3:15]O>>[O:1]=[C:2]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:15])=[O:8])[CH2:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2277983-Oxocyclopentanecarboxylic acid

Product 1

HCID 2376403-Oxo-cyclopentanecarboxylic acid methyl esterYield 84%

Procedure

A solution of 3-oxocyclopentanecarboxylic acid (13.2 g, 103 mmol), MeOH (130 ml) and 98% sulfuric acid (0.1 ml) was heated under reflux with stirring for 1.5 h. The MeOH was evaporated in vacuo. The residue was dissolved in CH2Cl2 (100 ml) and was washed with 1% sodium bicarbonate (50 ml). The solvent was evaporated in vacuo to give the title compound as a liquid, 12.2 g (84% yield); ir (liq.) νmax : 1730-1740 cm-1 ; 1Hmr (CDCl3) δ: 3.71 (s, 3H, OMe), 3.2 (m, 1H, H-1) and 2.5-1.9 ppm (m, 6H, CH2).

Workup

  1. temperatureunder reflux
  2. customThe MeOH was evaporated in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2 (100 ml)
  4. washwas washed with 1% sodium bicarbonate (50 ml)
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-4f48f972e0ef4af09218079faf00695f
Source dataset
uspto-grants-1981_06
Patent number
US04272437

Reaction notes

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