Hydrochloric Acid → (4-(4-Methyl-3-pentenyl)-3-cyclohexenyl)acetic acid

HRID 2227099Notes

Reaction equation

HRID 2227099 reaction equation
[OH-:1].[Na+].[CH3:3][C:4]([CH3:17])=[CH:5][CH2:6][CH2:7][C:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]#N)[CH2:10][CH:9]=1.Cl.[OH2:19]>OO>[CH3:3][C:4]([CH3:17])=[CH:5][CH2:6][CH2:7][C:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([OH:19])=[O:1])[CH2:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 18471789(4-(4-Methyl-3-pentenyl)-3-cyclohexenyl)acetonitrile

Product 1

HCID 18471803(4-(4-Methyl-3-pentenyl)-3-cyclohexenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 784Hydrogen PeroxideSolvent

Procedure

To a solution of sodium hydroxide (10.5 g) in water (150 mL) and 30% hydrogen peroxide (50 mL) is added the nitrile 2A (R=4-Methyl-3-pentenyl) (10 g). The reaction mixture is stirred at reflux overnight. The reaction is then cooled to room temperature, and poured into a mixture of ice (30 g) and hydrochloric acid (22 mL). The acid product is extracted with ethyl acetate, and the combined organic layers are washed with brine and dried over magnesium sulfate. The solution is concentrated in vacuo.

Workup

  1. temperatureat reflux overnight
  2. extractionThe acid product is extracted with ethyl acetate
  3. washthe combined organic layers are washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solution is concentrated in vacuo

Sources & evidence

ORD record
ord-653a52b5aaee4cd8bec4f76a400e3192
Source dataset
uspto-grants-2002_07
Patent number
US06413448B1

Reaction notes

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