HCID 2611, compound → HCID 178509803, compound

HRID 2081151Notes

Reaction equation

HRID 2081151 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([CH2:15][OH:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[O-][Si]([O-])=O.[Mg+2].C1SC2C(NC(CC3SC=CC=3)=O)C(=O)N2C(C(O)=O)=C1C[N+]1C=CC=CC=1>ClCCl.C(OCC)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([CH:15]=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 2611HCID 2611, compoundHCID 61680MAGNESIUM SILICATE (synthetic)HCID 178418287HCID 178418287, compoundHCID 178509804HCID 178509804, compound

Product 1

HCID 178509803HCID 178509803, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

Trimethylsilyl chloride (305.6 g, 2.81 mol) was dropwise added to trans-4-methoxymethyl-1-(4-cyanophenyl)cyclohexane (322.5 g, 1.41 mol), sodium iodide (421.6 g, 2.81 mol) and acetonitrile (2.5 l), with stirring in nitrogen atmosphere at 35° C. over 30 minutes, followed by agitating the mixture for 20 minutes, cooling it 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), twice washing the chloroform solution with a 10% by weight aqueous solution of sodium thiosulfate (0.5 l), further three times washing with water (1 l), distilling off chloroform, and three times recrystallizing the residue from toluene (300 ml) for purification to obtain trans-4-(4-cyanophenyl)cyclohexylcarbinol (182.5 g, 0.848 mol). M.P.: 108.5-110.8° C. A solution of this trans-4-(4-cyanophenyl)cyclohexylcarbinol (107.6 g, 0.500 mol) in dichloromethane (0.7 l) was instantaneously added to a solution of pyridinium chlorochromate (161.7 g, 0.750 mol) in dichloromethane (1 l), prepared in advance, with stirring, at room temperature, followed by agitating the mixture at room temperature for 1.5 hour, adding diethyl ether (1 l) to the resulting reaction solution, and subjecting the supernatant to column chromatography using Florisil® (made by Floridin Co., Ltd.) as a filler to obtain trans-4-(4-cyanophenyl)cyclohexylcarbaldehyde (101.2 g, 0.474 mol).

Workup

  1. customprepared in advance
  2. stirringby agitating the mixture at room temperature for 1.5 hour
  3. customto the resulting reaction solution
  4. customto obtain trans-4-(4-cyanophenyl)cyclohexylcarbaldehyde (101.2 g, 0.474 mol)

Sources & evidence

ORD record
ord-66117e047a3045e780bbfab2335b27aa
Source dataset
uspto-grants-1993_02
Patent number
US05183587

Reaction notes

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