Water → 10-(4-Chlorophenyl)dec-9-enoic acid

HRID 5258Notes

Reaction equation

HRID 5258 reaction equation
C[O:2][C:3](=[O:20])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1.O.[OH-].[K+]>CO>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([CH:12]=[CH:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:20])=[O:2])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 5408894010-(4-Chlorophenyl)-dec-9-enoic acid methyl ester

Product 1

HCID 5440741310-(4-Chlorophenyl)dec-9-enoic acidYield 103.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.62 g of 10-(4-chlorophenyl)-dec-9-enoic acid methyl ester in 200 mL of 4:1 methanol:water is added 5.4 g of KOH. The solution is stirred for 2 hours and extracted three times with diethyl ether. The aqueous layer is acidified with concentrated hydrochloric acid, and extracted three times with diethyl ether. The organic layers are combined, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give a yellow oil. The residue is purified via flash chromatography on a 40 mm×150 mm silica column eluting with 40% ethyl acetate/hexane to give 1.6 g (100%) of pure 10-(4-chlorophenyl)dec-9-enoic acid as a mixture of E and Z isomers.

Workup

  1. extractionextracted three times with diethyl ether
  2. extractionextracted three times with diethyl ether
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a yellow oil
  8. customThe residue is purified via flash chromatography on a 40 mm×150 mm silica column
  9. washeluting with 40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-40ccf594098e4ab0b5c9d652ad28c8c9
Source dataset
uspto-grants-1993_09
Patent number
US05242945

Reaction notes

Loading…