Acetone Cyanohydrin → 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionitrile

HRID 1576177Notes

Reaction equation

HRID 1576177 reaction equation
[C-]#N.[Na+].BrC[C:6]1[CH:21]=[CH:20][C:9]2[C:10](=[O:19])[C:11]3[CH:18]=[CH:17]C=[CH:15][C:12]=3[CH:13]=[CH:14][C:8]=2[CH:7]=1.[CH3:22][C:23]([CH3:27])(O)[C:24]#[N:25]>CCOCC>[CH:15]1[C:12]2[CH:13]=[CH:14][C:8]3[CH:7]=[CH:6][CH:21]=[CH:20][C:9]=3[C:10](=[O:19])[C:11]=2[CH:18]=[CH:17][C:22]=1[CH:23]([CH3:27])[C:24]#[N:25]

Participants

5

Reactant 3

HCID 6406Acetone CyanohydrinHCID 8929Sodium CyanideHCID 123988192-bromomethyl-5H-dibenzo[a,d]cyclohepten-5-one

Product 1

HCID 214030952-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

12.0 Gm. of sodium cyanide and 6.0 gm. of 2-bromomethyl-5H-dibenzo[a,d]cyclohepten-5-one are stirred at 100°C. for 40 minutes in 150 ml. of acetone cyanohydrin. The mixture is cooled and poured into ether. The ethereal layer is washed with water, dried and evaporated. The residue is chromatographed on 350 gm. of silica gel, eluting with hexane/ethyl acetate (3:2) to obtain 8.8 gm., 78%, of 5H-dibenzo[a,d]cyclohepten-5-on-2-yl acetonitrile which is recrystallized from ethyl acetate/hexane, m.p. 119°-121°C. Use of 2-(α-bromoethyl)-5H-dibenzo[a,d]cyclohepten-5-one gives a similar yield of 2-(5H-dibenzo[a,d] cyclohepten-5-on-2-yl)propionitrile, m.p. 108°-109°C.

Workup

  1. temperatureThe mixture is cooled
  2. washThe ethereal layer is washed with water
  3. customdried
  4. customevaporated
  5. customThe residue is chromatographed on 350 gm
  6. washof silica gel, eluting with hexane/ethyl acetate (3:2)
  7. customto obtain 8.8 gm
  8. custom, 78%, of 5H-dibenzo[a,d]cyclohepten-5-on-2-yl acetonitrile which is recrystallized from ethyl acetate/hexane, m.p. 119°-121°C

Sources & evidence

ORD record
ord-7f9958b7c57f4c1988112de076a7fe01
Source dataset
uspto-grants-1976_09
Patent number
US03979430

Reaction notes

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