Methanol → Methyl 1-hydroxycyclopentane-1-carboxylate

HRID 1672289Notes

Reaction equation

HRID 1672289 reaction equation
[OH:1][C:2]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.S(=O)(=O)(O)O.[CH3:15]O>>[OH:1][C:2]1([C:7]([O:9][CH3:15])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Procedure

To a solution of 1-hydroxycyclopentanecarboxylic acid (2.00 g) in methanol (15 mL) was added conc. sulfuric acid (0.1 mL), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo, and the resultant residue was diluted with diethylether. The mixture was washed successively with an aqueous saturated sodium hydrogencarbonate solution and brine. The organic layer was dried over sodium sulfate and concentrated in vacuo to give methyl 1-hydroxy-cyclopentanecarboxylate (2.06 g) as a pale brown oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe resultant residue was diluted with diethylether
  3. washThe mixture was washed successively with an aqueous saturated sodium hydrogencarbonate solution and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-052b6150cd704e2fa4aca3967c8afb50
Source dataset
uspto-grants-2011_08
Patent number
US07998956B2

Reaction notes

Loading…