Potassium Hydroxide → 7-(2-Hexyl-5-keto-cyclopentyl)-heptanoic acid

HRID 330105Notes

Reaction equation

HRID 330105 reaction equation
[OH-].[K+].[CH2:3]([CH:9]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23]C)=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>CO>[CH2:3]([CH:9]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 214205217-(2-Hexyl-5-keto-cyclopentyl)-heptanoic acid, methyl ester

Product 1

HCID 146371057-(2-Hexyl-5-keto-cyclopentyl)-heptanoic acidYield 27.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A potassium hydroxide (15 g, 0.27 mole) solution in methanol (30 ml) is added with a solution of ester (VIII) (50 g, 0.16 mole) in methanol (120 g). The reaction mixture is refluxed for 2 hours. It is then cooled and concentrated under reduced pressure, poured into water (200 ml) and acidified with conc. hydrochloric acid. It is then extracted with ethyl acetate (3×100 ml). The acid (IX) (13 g) is obtained. Yield=27%.

Workup

  1. temperatureThe reaction mixture is refluxed for 2 hours
  2. temperatureIt is then cooled
  3. concentrationconcentrated under reduced pressure
  4. additionpoured into water (200 ml)
  5. extractionIt is then extracted with ethyl acetate (3×100 ml)

Sources & evidence

ORD record
ord-99b82ab9733b40c980cdfb6417517fc8
Source dataset
uspto-grants-1990_01
Patent number
US04894473

Reaction notes

Loading…