Methanol → Methyl 1-hydroxycyclopentane-1-carboxylate

HRID 626532Notes

Reaction equation

HRID 626532 reaction equation
[OH:1][C:2]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:10]O>OS(O)(=O)=O>[OH:1][C:2]1([C:7]([O:9][CH3:10])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 887MethanolHCID 1171771-Hydroxycyclopentanecarboxylic acid

Product 1

HCID 244662Methyl 1-hydroxycyclopentane-1-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
65 °C

Procedure

A solution of 1-hydroxycyclopentanecarboxylic acid (1.4 g, 10.76 mmol) in MeOH (10 mL) was treated with conc. H2SO4 (1 drop), heated at 65° C. for 2 h, cooled to RT and concentrated to dryness. The residue was treated with satd. NaHCO3, extracted with DCM (3×) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford methyl 1-hydroxycyclopentanecarboxylate (1.45 g, 92%). 1H NMR (400 MHz, CDCl3): δ 3.79 (s, 3H), 2.92 (br s, 1H), 2.11-2.00 (m, 2H), 1.91-1.83 (m, 2H), 1.82-1.72 (m, 4H).

Workup

  1. temperaturecooled to RT
  2. concentrationconcentrated to dryness
  3. additionThe residue was treated with satd
  4. extractionNaHCO3, extracted with DCM (3×)
  5. washthe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f309a53ba4644ddfa0ab1f7e4fc8b474
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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