Ethylene Glycol → γ,γ,4-Trimethylbenzenebutanoic acid

HRID 1833939Notes

Reaction equation

HRID 1833939 reaction equation
[OH-:1].[K+].[CH3:3][C:4]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)([CH3:9])[CH2:5]CC#N.Cl.[CH2:18]([OH:21])[CH2:19]O>[Cu]>[CH3:3][C:4]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)([CH3:9])[CH2:5][CH2:19][C:18]([OH:21])=[O:1]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 21388143HCID 21388143, compound

Product 1

HCID 10878311γ,γ,4-Trimethylbenzenebutanoic acidYield 89.6%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
10 °C

Procedure

Potassium hydroxide (112 g) is slowly dissolved (heat evolved) in ethylene glycol (400 ml) in a 2 liter copper (or stainless steel) flask. The 4-methyl-4-p-tolylpentanenitrile (94 g, 0.5 mol) was then added, the mixture refluxed for 6 hours, cooled to 10° C and diluted with 400 ml ice cold water. Hydrochloric acid (conc., 180 ml) was added slowly (heat evolved, cooling required) until the reaction mixture was acid to congo test paper. The resulting mixture was extracted with benzene, washed with water, concentrated and distilled to yield 92.8 g (89.6%) of the 4-methyl-4-p-tolylpentanoic acid: bp 178° (2 mm); nD20 1.5147;

Workup

  1. temperaturethe mixture refluxed for 6 hours
  2. temperature(heat evolved, cooling required) until the reaction mixture
  3. extractionThe resulting mixture was extracted with benzene
  4. washwashed with water
  5. concentrationconcentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-783b8cf7f1b84000a3a96c8acce0a3e4
Source dataset
uspto-grants-1978_01
Patent number
US04067906

Reaction notes

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