Hydrochloric Acid → HCID 178444340, compound

HRID 2254976Notes

Reaction equation

HRID 2254976 reaction equation
[CH:1](/[C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:19]=[CH:18]C(C#N)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[CH:2]\[CH2:3][CH2:4][CH3:5].[OH-:20].[K+].Cl.C(O)CO[CH2:26][CH2:27][OH:28]>O>[CH:1](/[C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:19]=[CH:18][C:26]([C:27]([OH:28])=[O:20])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[CH:2]\[CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 178444327HCID 178444327, compound

Product 1

HCID 178444340HCID 178444340, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.1 g of p-[trans-4-(1E-pentenyl)cyclohexyl]benzonitrile were boiled at 180° C. for 16 hours while gassing with argon in 17.5 ml of a 10 percent solution of potassium hydroxide in diethylene glycol. After cooling to room temperature the dark brown reaction mixture was diluted with 20 ml of water, made acid with 25 percent hydrochloric acid and extracted four times with 100 ml of ethylene chloride each time. The organic phases were washed twice with 80 ml of water each time, dried over magnesium suphate and active carbon and concentrated. There were obtained 1.16 g (98%) of p-[trans-4-(1E-pentenyl)cyclohexyl]benzoic acid as beige crystals; Rf-value (toluene/ethyl acetate vol. 3:1) 0.45.

Workup

  1. customfor 16 hours
  2. extractionextracted four times with 100 ml of ethylene chloride each time
  3. washThe organic phases were washed twice with 80 ml of water each time
  4. dry with materialdried over magnesium suphate and active carbon
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-027ad8efc08549feb1891f95e0e1a049
Source dataset
uspto-grants-1993_08
Patent number
US05238602

Reaction notes

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