Ammonia → HCID 178445626, compound

HRID 2254940Notes

Reaction equation

HRID 2254940 reaction equation
[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][C:12]#N)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[OH-:14].[K+].N.C1C=CC2C(C3C=CC(O)=CC=3)(C3C=CC(O)=CC=3)OC(=[O:24])C=2C=1>C(O)C.O>[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][C:12]([OH:24])=[O:14])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 222Ammonia2×HCID 4764PhenolphthaleinHCID 14797Potassium HydroxideHCID 178445620HCID 178445620, compound

Product 1

HCID 178445626HCID 178445626, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 34 g (0.19 mol) of trans-4-butylcyclohexyl acetonitrile, 43 g (0.76 mol) of KOH, and 34 cm3 of water in 190 cm3 of ethanol was refluxed over a hot water bath until the generation of ammonia gas ceased (about 10 hours). Ammonia gas was detected using phenolphthalein test paper. The reaction solution was cooled to room temperature and ethanol was distilled off. The residue was dissolved in 100 cm3 of water. The resulting solution was poured into a beaker containing 100 g of water and 100 cm3 of concentrated hydrochloric acid. The crystals precipitated in the beaker were separated out by filtration and washed with water. The crystals were recrystallized from a solvent mixture of methanol and water to yield 37 g (0.19 mol) of trans-4-butylcyclohexyl acetic acid.

Workup

  1. custom(about 10 hours)
  2. distillationethanol was distilled off
  3. dissolutionThe residue was dissolved in 100 cm3 of water
  4. additionThe resulting solution was poured into a beaker
  5. additioncontaining 100 g of water and 100 cm3 of concentrated hydrochloric acid
  6. customThe crystals precipitated in the beaker
  7. customwere separated out by filtration
  8. washwashed with water
  9. customThe crystals were recrystallized from a solvent mixture of methanol and water

Sources & evidence

ORD record
ord-85f181835aba4af6b76bcbb082066fc8
Source dataset
uspto-grants-1993_08
Patent number
US05238599

Reaction notes

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