Potassium Hydroxide → [5-(3-Methylbutoxy)-2-propylphenylthio] fumaric acid

HRID 1606106Notes

Reaction equation

HRID 1606106 reaction equation
[CH3:1][CH:2]([CH3:16])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:13][CH2:14][CH3:15])=[C:10]([SH:12])[CH:11]=1.[OH-].[K+].[K+].[C:20]([C:25]([O-:27])=[O:26])#[C:21][C:22]([OH:24])=[O:23]>O>[CH3:1][CH:2]([CH3:16])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:13][CH2:14][CH3:15])=[C:10]([S:12]/[C:21](=[CH:20]\[C:25]([OH:27])=[O:26])/[C:22]([OH:24])=[O:23])[CH:11]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 215459855-(3-Methylbutoxy)-2-propylthiophenolHCID 236779642-Butynedioic acid, monopotassium salt

Product 1

HCID 86733255[5-(3-Methylbutoxy)-2-propylphenylthio] fumaric acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 95.7 parts of 5-(3-methylbutoxy)-2-propylthiophenol, 54 parts of potassium hydroxide and 73 parts of acetylene dicarboxylic acid mono potassium salt in 350 parts of water was refluxed for 40 minutes and cooled. The mixture was filtered through Whatman 54 filter paper to remove an oil residue and the filtrate was acidified to pH 1 with concentrated hydrochloric acid. The resulting yellow precipitate was collected, washed with water and dried in vacuo to give 67.8 parts of the desired product as a yellow powder, mp 121° - 129°C Crystallization from 15% ethanol-water afforded pure [5-(3-methylbutoxy)-2-propylphenylthio] fumaric acid, m.p. 131° - 133°C.

Workup

  1. temperaturecooled
  2. filtrationThe mixture was filtered through Whatman 54
  3. filtrationfilter paper
  4. customto remove an oil residue
  5. customThe resulting yellow precipitate was collected
  6. washwashed with water
  7. customdried in vacuo
  8. customto give
  9. custom67.8 parts of the desired product as a yellow powder, mp 121° - 129°C Crystallization from 15% ethanol-water afforded pure [5-(3-methylbutoxy)-2-propylphenylthio] fumaric acid, m.p. 131° - 133°C.

Sources & evidence

ORD record
ord-ee2496d876034faaab063a1b7e507f35
Source dataset
uspto-grants-1976_04
Patent number
US03952013

Reaction notes

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