Ethanol → HCID 18319112, compound

HRID 1383946Notes

Reaction equation

HRID 1383946 reaction equation
COC(=O)[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][S:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:8][CH:7]=1)[CH3:5].[OH-:29].[K+].[CH2:31]([OH:33])C>O>[CH2:16]([S:15][CH2:14][CH2:13][O:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:4][CH2:5][C:31]([OH:33])=[O:29])=[CH:11][CH:10]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 54496833HCID 54496833, compound

Product 1

HCID 18319112HCID 18319112, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A suspension of 2-[4-[2-(dodecylthio)ethoxy]phenyl]propanoic acid methyl ester (4.70 g, 11.5 mmol) in 80% ethanol (100 ml) was treated with a solution of potassium hydroxide (1.33 g, 20.1 mmol) in water (10 ml) and the mixture was stirred at 55° C. for 1 h. The solvent was then concentrated in vacuo and the residue was diluted with water (100 ml) and dichloromethane (250 ml). The solution was then adjusted to pH 2 with diluted hydrochloric acid and the aqueous phase was extracted a second time with dichloromethane. The combined organic extracts were washed with brine and dried (magnesium sulfate). Evaporation of the solvent under reduced pressure and crystallization of the residue from ethyl acetate-hexane gave 3.56 g (78%) of 3-[4-[2-(dodecylthio)ethoxy]phenyl]propanoic acid as white prisms: m.p. 68-69° C.

Workup

  1. concentrationThe solvent was then concentrated in vacuo
  2. additionthe residue was diluted with water (100 ml) and dichloromethane (250 ml)
  3. extractionthe aqueous phase was extracted a second time with dichloromethane
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. customEvaporation of the solvent
  7. customunder reduced pressure and crystallization of the residue from ethyl acetate-hexane

Sources & evidence

ORD record
ord-4807e197b4454ffe90130480d9fc7a49
Source dataset
uspto-grants-2001_07
Patent number
US06255496B1

Reaction notes

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