Lithium Hydroxide → 1-Methoxycyclopentane-1-carboxylic acid

HRID 626534Notes

Reaction equation

HRID 626534 reaction equation
[CH3:1][O:2][C:3]1([C:8]([O:10]C)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1.[Li+].[OH-]>C1COCC1.O>[CH3:1][O:2][C:3]1([C:8]([OH:10])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67529636Methyl 1-methoxycyclopentane-1-carboxylate

Product 1

HCID 205670831-Methoxycyclopentane-1-carboxylic acidYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 1-methoxycyclopentanecarboxylate (1.00 g, 6.32 mmol) in THF (10 mL) was treated with a solution of LiOH (0.531 g, 12.64 mmol) in water (5 mL), stirred at RT overnight and concentrated to dryness. The residue was diluted with water, acidified with HCl (2M, 6 mL), extracted with EtOAc (3×) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford 1-methoxycyclopentanecarboxylic acid (900 mg, 99%). 1H NMR (400 MHz, CDCl3): δ 3.31 (s, 3H), 2.05-2.03 (m, 4H), 1.78-1.77 (m, 4H) [CO2H not observed].

Workup

  1. concentrationconcentrated to dryness
  2. additionThe residue was diluted with water
  3. extractionextracted with EtOAc (3×)
  4. washthe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a920a9afa8b640f0bfee527daaac0d97
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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