Lithium Hydroxide → 1-Methoxycyclopentane-1-carboxylic acid
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]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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
- concentrationconcentrated to dryness
- additionThe residue was diluted with water
- extractionextracted with EtOAc (3×)
- washthe combined organics were washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-8826dedbd6d246c990326a99925602e8
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382228B2
Reaction notes
Loading…