Water → 5-methoxypentanoic Acid
Reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9]C)=[O:8].[OH-].[K+].O>CO>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Methyl 5-methoxyvalerate (7.33 g, 50.2 mmol) and KOH (14.4 g, 0.256 mol) were dissolved into a mixture of 50 ml of water and 150 ml of MeOH. The solution was stirred at 0° C. for 2 hrs then MeOH was removed in vacuo. After washed by CHCl3 (50 ml), the aqueous layer was acidified to pH=1 by 2N HCl and extracted by Et2O (2×100 ml). Organic layers were combined, washed with water (100 ml) and dried over Na2 SO4. After filtration and evaporation of solvent, 5-methoxyvaleric acid (5.27 g, 79.6%) was obtained as a colorless oil.
Workup
- customMeOH was removed in vacuo
- washAfter washed by CHCl3 (50 ml)
- extractionextracted by Et2O (2×100 ml)
- washwashed with water (100 ml)
- customdried over Na2 SO4
- filtrationAfter filtration and evaporation of solvent
Sources & evidence
- ORD record
- ord-686be116e0264cc78a3d3b912c857e1e
- Source dataset
- uspto-grants-1998_06
- Patent number
- US05767131
Reaction notes
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