Water → HCID 178447875, compound

HRID 1589742Notes

Reaction equation

HRID 1589742 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:18]=[CH:17][C:13]([CH2:14][C:15]#N)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[OH2:19].[OH-:20].[K+]>CO>[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:18]=[CH:17][C:13]([CH2:14][C:15]([OH:20])=[O:19])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 178447873HCID 178447873, compound

Product 1

HCID 178447875HCID 178447875, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

106 g (0.44 mol) of 4-(trans-4'-propylcyclohexyl) benzyl cyanide, 40 g of water, 145 g (2.2 mol) of KOH and 440 cm3 of methanol were refluxed for 10 hours using a mantle heater. The ethanol was distilled off under reduced pressure. The residue was dissolved in 300 cm3 of water and poured into 300 cm3 of concentrated hydrochloric acid and 300 g of ice. The crystals deposited were filtered out and washed with cold water. The crystals were recrystallized from methanol to yield 112 g (0.43 mol) of 4-(trans-4'-propylcyclohexyl)phenyl acetic acid.

Workup

  1. distillationThe ethanol was distilled off under reduced pressure
  2. dissolutionThe residue was dissolved in 300 cm3 of water
  3. additionpoured into 300 cm3 of concentrated hydrochloric acid and 300 g of ice
  4. filtrationThe crystals deposited were filtered out
  5. washwashed with cold water
  6. customThe crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-af198656fdec4b6d8e75434dfa446362
Source dataset
uspto-grants-1993_04
Patent number
US05200110

Reaction notes

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