Water → 5-methoxypentanoic Acid

HRID 322202

Reaction equation

HRID 322202 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

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 Na2SO4. After filtration and evaporation of solvent, 5-methoxyvaleric acid (5.27 g, 79.6%) was obtained as a colorless oil.

Workup

  1. customMeOH was removed in vacuo
  2. washAfter washed by CHCl3 (50 ml)
  3. extractionextracted by Et2O (2×100 ml)
  4. washwashed with water (100 ml)
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration and evaporation of solvent

Sources & evidence

ORD record
ord-2a53df0522c64def855bf4dce4e18bb4
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Linked notes

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