Methanol → 4-(4-Formyl-4-propylcyclohexyl)-4'-pentylbiphenyl

HRID 704283Notes

Reaction equation

HRID 704283 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([C:13]1([CH2:36][CH2:37][CH3:38])[CH2:18][CH2:17][CH:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)[CH2:15][CH2:14]1)#N.C[OH:40]>CCCCCC>[CH:11]([C:13]1([CH2:36][CH2:37][CH3:38])[CH2:18][CH2:17][CH:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)[CH2:15][CH2:14]1)=[O:40]

Participants

5

Reactant 3

HCID 887MethanolHCID 135612474-(4-Cyano-4-propylcyclohexyl)-4'-pentylbiphenylHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 135612484-(4-Formyl-4-propylcyclohexyl)-4'-pentylbiphenyl

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

55 ml of a 1M solution of diisobutyl-aluminium hydride (DIBAH) in n-hexane are added to a solution of 8.6 g (0.05 mole) of 4-(4-cyano-4-propyl-cyclohexyl)-4'-n-pentylbiphenyl (Example 1) in 100 ml of hexane at 0°, under a nitrogen atmosphere and with exclusion of moisture. The mixture is stirred at room temperature for one hour and 5 ml of methanol are then carefully added. The reaction mixture is poured into 200 ml of ice-cold 10% H2SO4 and stirred for 30 minutes. The organic phase is then separated off and the aqueous phase is extracted twice more with hexane. The combined organic phases are neutralised with NaHCO3 solution and then dried. Purification by chromatography gives 4-(4-formyl-4-propylcyclohexyl)-4'-pentylbiphenyl.

Workup

  1. stirringstirred for 30 minutes
  2. customThe organic phase is then separated off
  3. extractionthe aqueous phase is extracted twice more with hexane
  4. customdried
  5. customPurification by chromatography

Sources & evidence

ORD record
ord-f9c404f7a6c14d11b2699019837d8850
Source dataset
uspto-grants-1991_01
Patent number
US04985583

Reaction notes

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