Sodium Chloride → Trans-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]5-cyanocyclohexanone

HRID 1650050Notes

Reaction equation

HRID 1650050 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:10]=1[CH:24]1[CH2:29][C:28](=[O:30])[CH:27]=[CH:26][CH2:25]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.[C-:37]#[N:38].[K+].[Cl-].[Na+]>CCOCC.C(O)C.O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:22])([CH3:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:10]=1[C@H:24]1[CH2:25][C@H:26]([C:37]#[N:38])[CH2:27][C:28](=[O:30])[CH2:29]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 9032Potassium Cyanide2×HCID 127882935-(2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-2-cyclohexen-1-one

Product 1

HCID 13105260Trans-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]5-cyanocyclohexanoneYield 71%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a refluxing solution of 3.99 g. (9.87 mmole) of 5-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-2-cyclohexen-1-one in 6.65 ml. of ethyl acetate was added a hot solution of 800 mg. (11.9 mmole) of potassium cyanide in 2 ml. water and 2.3 ml. ethanol. The reaction was refluxed 2 hours and then another 2.74 mmole of potassium cyanide added. The reaction was refluxed one hour longer and then cooled and added to 400 ml. saturated sodium chloride-400 ml. ether. The ether extract was dried over magnesium sulfate and evaporated to yield an oil. The crude oil was purified via column chromatography on 160 g. of silica gel eluted with 10% acetone-hexane to yield 3.02 g. (71%) of the title compound.

Workup

  1. temperatureThe reaction was refluxed 2 hours
  2. temperatureThe reaction was refluxed one hour longer
  3. temperaturecooled
  4. additionadded to 400 ml
  5. extractionThe ether extract
  6. dry with materialwas dried over magnesium sulfate
  7. customevaporated
  8. customto yield an oil
  9. customThe crude oil was purified via column chromatography on 160 g
  10. washof silica gel eluted with 10% acetone-hexane
  11. customto yield 3.02 g

Sources & evidence

ORD record
ord-18cf924a1202470098e7a24ee5161c50
Source dataset
uspto-grants-1990_05
Patent number
US04921994

Reaction notes

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