Sulfuric Acid → HCID 178444410, compound

HRID 370674Notes

Reaction equation

HRID 370674 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13][C:14]2[CH:21]=[CH:20][C:17]([C:18]#N)=[CH:16][CH:15]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[H-].C([Al+]CC(C)C)C(C)C.S(=O)(=O)(O)[OH:33]>C1(C)C=CC=CC=1>[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13][C:14]2[CH:21]=[CH:20][C:17]([CH:18]=[O:33])=[CH:16][CH:15]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 21225700DiisobutylaluminumhydrideHCID 178444408HCID 178444408, compound

Product 1

HCID 178444410HCID 178444410, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 7.08 g of p-[2-(trans-4-pentylcyclohexyl)ethyl]benzonitrile in 50 ml of absolute toluene was placed at 0° C. in a sulphonation flask under argon gasification and treated within 15 minutes with 29 ml of a 1.21N solution of diisobutylaluminium hydride in toluene in such a manner that the internal temperature did not exceed 5° C. After completion of the addition, the mixture was stirred at room temperature for a further 2 hours, then treated cautiously with 50 ml of 0.5N sulphuric acid and extracted three times with 100 ml of diethyl ether each time. The organic phases were washed twice with 50 ml of semi-saturated sodium chloride solution each time, dried over magnesium sulphate and concentrated. There were obtained 6.20 g (87%) of p-[2-(trans-4-pentylcyclohexyl)ethyl]benzaldehyde as a colourless viscous oil (purity 97%) which was used without additional purification.

Workup

  1. customdid not exceed 5° C
  2. additionAfter completion of the addition
  3. extractionextracted three times with 100 ml of diethyl ether each time
  4. washThe organic phases were washed twice with 50 ml of semi-saturated sodium chloride solution each time
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-30190c9c47bb4bec91501724b7dfdcf8
Source dataset
uspto-grants-1985_07
Patent number
US04528114

Reaction notes

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