Benzyl Alcohol → HCID 20269563, compound

HRID 485767Notes

Reaction equation

HRID 485767 reaction equation
[CH:1]1(/[CH:7]=[CH:8]/[C:9]#[N:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:11]([OH:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[Na].CCOCC>[CH2:11]([O:18][CH:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH2:8][CH2:9][NH2:10])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 244Benzyl AlcoholHCID 538261222031-57-8

Product 1

HCID 20269563HCID 20269563, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 5360545SodiumSolvent2×

Procedure

The foregoing mixture of 2-cis and 2-trans-3-cyclohexylacrylonitrile (26.50 g) was dissolved in sodium benzylate solution prepared from sodium (0.65 g) and benzyl alcohol (90 ml) and the resulting solution heated on the steam-bath with stirring for 4 hours then set aside at room temperature for 18 hours. The resulting dark solution was diluted with ether and washed with water. The ethereal extract was dried (Na2SO4), the solvent removed in vacuo, and the residual unchanged nitrile removed by distillation under high vacuum. The residual material was taken up in ether, colorised with activated charcoal, filtered, and the solvent removed in vacuo. The residual yellow syrup (ca. 22 g) was dissolved in dry ether (40 ml) and added dropwise at +5° to a stirred suspension of lithium aluminium hydride (3.4 g) in dry ether (125 ml). After 1 hour at room temperature, the reaction mixture was treated with water and the resulting gel filtered through Celite. The yellow organic phase was separated, dried (MgSO4), the solvent removed in vacuo, and the residual orange oil distilled, giving 3-benzyloxy-3-cyclohexylpropylamine as a colourless viscous oil. b.p. 120°-5°/0.05-0.06 mm.

Workup

  1. temperaturethe resulting solution heated on the steam-bath
  2. waitthen set aside at room temperature for 18 hours
  3. washwashed with water
  4. extractionThe ethereal extract
  5. dry with materialwas dried (Na2SO4)
  6. customthe solvent removed in vacuo
  7. customthe residual unchanged nitrile removed by distillation under high vacuum
  8. filtrationfiltered
  9. customthe solvent removed in vacuo
  10. dissolutionThe residual yellow syrup (ca. 22 g) was dissolved in dry ether (40 ml)
  11. additionadded dropwise at +5° to a stirred suspension of lithium aluminium hydride (3.4 g) in dry ether (125 ml)
  12. waitAfter 1 hour at room temperature
  13. additionthe reaction mixture was treated with water
  14. filtrationthe resulting gel filtered through Celite
  15. customThe yellow organic phase was separated
  16. dry with materialdried (MgSO4)
  17. customthe solvent removed in vacuo
  18. distillationthe residual orange oil distilled

Sources & evidence

ORD record
ord-20e51138383945e0b2ab1368e09c120c
Source dataset
uspto-grants-1985_08
Patent number
US04537972

Reaction notes

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