Water → [1,1'-Biphenyl]-4-carboxaldehyde, 4'-pentyl-
Reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#N)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[H-].C([Al+]CC(C)C)C(C)C.S(=O)(=O)(O)[OH:31].O>C1(C)C=CC=CC=1>[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]=[O:31])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 10 g of 4-pentyl-4'-cyanobiphenyl in 150 ml of toluene was treated dropwise at 0° C. with 65 ml of a 1M solution of diisobutylaluminium hydride in toluene while gassing with nitrogen. The reaction mixture was stirred at room temperature overnight, then treated dropwise with 340 ml of 1N sulphuric acid, stirred at room temperature for 1 hour, poured into 1,000 ml of water and then extracted three times with 100 ml of ethyl acetate each time. The combined organic phases were washed twice with 50 ml of saturated sodium chloride solution each time, dried over magnesium sulphate, filtered and subsequently concentrated. Chromatographic purification of the residue on silica gel with hexane/ethyl acetate (vol. 9:1) gave 10.1 g of 4-pentyl-4'-biphenylcarboxaldehyde.
Workup
- stirringstirred at room temperature for 1 hour
- extractionextracted three times with 100 ml of ethyl acetate each time
- washThe combined organic phases were washed twice with 50 ml of saturated sodium chloride solution each time
- dry with materialdried over magnesium sulphate
- filtrationfiltered
- concentrationsubsequently concentrated
- customChromatographic purification of the residue on silica gel with hexane/ethyl acetate (vol. 9:1)
Sources & evidence
- ORD record
- ord-875317b314054938868ca628d59b6795
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05539074
Reaction notes
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