Sulfuric Acid → [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]>C1(C)C=CC=CC=1>[CH:18]([C:15]1[CH:16]=[CH:17][C:12]([C:9]2[CH:10]=[CH:11][C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:7][CH:8]=2)=[CH:13][CH:14]=1)=[O:31]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 6.23 g of 4'-pentyl-4-cyanobiphenyl in 50 ml of absolute toluene was placed at 0° C. in a sulphonation flask under argon gasification and treated within 10 minutes with 27 ml of a 1.36N solution of diisobutylaluminium hydride in toluene. After completion of the addition, the mixture was stirred at room temperature for a further 22 hours, then poured cautiously into 50 ml of 1N sulphuric acid and extracted three times with 100 ml of diethyl ether each time. The organic phases were washed once with 50 ml of 1N sulphuric acid and twice with 50 ml of water each time, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the oily residue (6.0 g on silica gel with 10% ethyl acetate/petroleum ether gave 5.86 g (93%) of 4-formyl-4'-pentylbiphenyl as a colourless viscous oil (purity 99.7%).
Workup
- additionAfter completion of the addition
- extractionextracted three times with 100 ml of diethyl ether each time
- washThe organic phases were washed once with 50 ml of 1N sulphuric acid and twice with 50 ml of water each time
- dry with materialdried over magnesium sulphate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-28276fdf7d674eb2afe455ffda15096f
- Source dataset
- uspto-grants-1985_07
- Patent number
- US04528114
Reaction notes
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