Hydrochloric Acid → 2-(4-n-Propylphenylthio)nonanoic acid

HRID 2257158

Reaction equation

HRID 2257158 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH:11]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:12]([O:14]CC)=[O:13])=[CH:6][CH:5]=1)[CH2:2][CH3:3].[OH-].[Na+].Cl>CO>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH:11]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:12]([OH:14])=[O:13])=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14995384Ethyl 2-(4-n-Propylphenylthio)nonanoate

Product 1

HCID 149953862-(4-n-Propylphenylthio)nonanoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution containing 5.7 (0.017 mole) of the title compound of Example 1, 35 ml of 1N aqueous sodium hydroxide solution (0.035 mole) and 3 ml methanol was refluxed overnight. The resulting solution was cooled to room temperature, acidified to pH 1.5 with 2N aqueous hydrochloric acid and extracted with 3×50 ml ethyl acetate. The combined ethyl acetate extracts were washed with 50 ml water and 50 ml saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo to yield the title compound as an oil (5.0 g, 96% yield) which was used in the subsequent reaction without further purification.

Workup

  1. temperaturewas refluxed overnight
  2. extractionextracted with 3×50 ml ethyl acetate
  3. washThe combined ethyl acetate extracts were washed with 50 ml water and 50 ml saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e724042210d34632af98c871d08c3b04
Source dataset
uspto-grants-1997_08
Patent number
US05656634

Linked notes

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