Potassium Hydroxide → HCID 18319089, compound

HRID 1383949Notes

Reaction equation

HRID 1383949 reaction equation
[OH:1][CH2:2][CH2:3][S:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([O:18]C)=[O:17])=[CH:10][CH:9]=1.[OH-].[K+]>C(O)C.O>[OH:1][CH2:2][CH2:3][S:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22949955HCID 22949955, compound

Product 1

HCID 18319089HCID 18319089, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
22 °C

Procedure

A solution of 3-[4-[2-(2-hydroxyethylthio)ethoxy]phenyl]propanoic acid, methyl ester (37.64 g, 0.132 mol) in 80% aqueous ethanol (300 ml) was treated with a solution of potassium hydroxide (17.0 g, 0.257 mol) in water (25 ml) and the resulting mixture was stirred at 22° C. for 1 h. The solvent was then concentrated in vacuo and the residue was diluted with water (200 ml) and dichloromethane (200 ml). The aqueous phase was then adjusted to pH 2 with 6N hydrochloric acid and extracted several times with dichloromethane. The combined organic extracts were washed with brine, dried (magnesium sulfate) and evaporated to give 35.67 g (100%) of the title material as a white solid: mp 64-65° C.

Workup

  1. concentrationThe solvent was then concentrated in vacuo
  2. additionthe residue was diluted with water (200 ml) and dichloromethane (200 ml)
  3. extractionextracted several times with dichloromethane
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated

Sources & evidence

ORD record
ord-0a758484f2e44a6abe3a8933984db176
Source dataset
uspto-grants-2001_07
Patent number
US06255496B1

Reaction notes

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