Sodium Iodide → HCID 178509804, compound

HRID 1638493Notes

Reaction equation

HRID 1638493 reaction equation
C[Si](Cl)(C)C.C[O:7][CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1.[Na+].[I-]>C(#N)C>[C:21]([C:18]1[CH:19]=[CH:20][C:15]([C@H:12]2[CH2:13][CH2:14][C@H:9]([CH2:8][OH:7])[CH2:10][CH2:11]2)=[CH:16][CH:17]=1)#[N:22]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 178495621HCID 178495621, compound

Product 1

HCID 178509804HCID 178509804, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
35 °C

Procedure

Trimethylsilyl chloride (305.6 g, 2.81 mols) was dropwise added to trans-4-methoxymethyl-1-(4-cyanophenyl)-cyclohexane (III) (322.5 g, 1.41 mol), NaI (421.6 g, 2.81 mols) and acetonitrile (2.5 l) in nitrogen atmosphere with stirring at 35° C. over 30 minutes, followed by agitating the mixture for 20 minutes, cooling down to 10° C., filtering the reaction mixture by suction, pouring the mother liquor in ice water (2 Kg), extracting with chloroform (1.5 l), subjecting the resulting chloroform solution to twice washing with a 10% by weight aqueous solution of thiosulfate (0.5 l) and separating, further three times subjecting to washing with water (1 l) and separating, distilling off chloroform and three times recrystallizing the residue from toluene (300 ml) to obtain trans-4-(4-cyanophenyl)-cyclohexylcarbinol (IV) (182.5 g, 0.848 mol) having a m.p. of 108.5°-110.8° C. On the other hand, pyridinium chlorochromate (161.7 g, 0.750 mol) was added to dichloromethane (1 l), followed by instantaneously adding to the solution a solution of trans-4-(4-cyanophenyl)cyclohexylcarbinol (IV) (107.6 g, 0.500 mol) obtained above (107.6 g, 0.500 mol) in dichloromethane (0.7 l) with stirring at room temperature, further agitating the mixture at room temperature for 1.5 hour, adding diethyl ether (1 l) to the resulting reaction solution and concentrating the supernatant according to florysil column chromatography to obtain trans-4-(4-cyanophenyl)cyclohexylcarboaldehyde (V) (101.2 g, 0.474 mol).

Workup

  1. stirringby agitating the mixture for 20 minutes
  2. temperaturecooling down to 10° C.
  3. filtrationfiltering the reaction mixture by suction
  4. additionpouring the mother liquor in ice water (2 Kg)
  5. extractionextracting with chloroform (1.5 l)
  6. washto twice washing with a 10% by weight aqueous solution of thiosulfate (0.5 l)
  7. customseparating
  8. washto washing with water (1 l)
  9. customseparating
  10. distillationdistilling off chloroform and three times
  11. customrecrystallizing the residue from toluene (300 ml)

Sources & evidence

ORD record
ord-ee0e1135db1a4665a8de0b5dd5258ab4
Source dataset
uspto-grants-1989_11
Patent number
US04880562

Reaction notes

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