Sulfuric Acid → HCID 178447982, compound

HRID 1249304Notes

Reaction equation

HRID 1249304 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]([C@H:14]1[CH2:19][CH2:18][C@H:17]([CH2:20][CH2:21][C@H:22]2[CH2:27][CH2:26][C@H:25]([C:28]#N)[CH2:24][CH2:23]2)[CH2:16][CH2:15]1)[CH2:12][CH3:13].S(=O)(=O)(O)[OH:31]>C1(C)C=CC=CC=1>[CH2:11]([C@H:14]1[CH2:19][CH2:18][C@H:17]([CH2:20][CH2:21][C@H:22]2[CH2:27][CH2:26][C@H:25]([CH:28]=[O:31])[CH2:24][CH2:23]2)[CH2:16][CH2:15]1)[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 21225700DiisobutylaluminumhydrideHCID 178447981HCID 178447981, compound

Product 1

HCID 178447982HCID 178447982, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

24 ml of a 1.2M solution of diisobutylaluminium hydride in toluene were added dropwise over a period of 30 minutes at 0° C. and under an inert gas atmosphere to a solution of 5.5 g of trans-4-[2-(trans-4-propylcyclohexyl)ethyl]cyclohexanecarbonitrile in 500 ml of toluene. The mixture was stirred at 0° C. for another hour and then at room temperature for 3 hours. The mixture was subsequently poured into 500 ml of 0.5N sulphuric acid and extracted three times with 200 ml of diethyl ether each time. The combined organic phases were washed first with saturated sodium hydrogen carbonate solution and then with water, dried over sodium sulphate and concentrated, thereby obtaining 5.6 g of trans-4-[2-(trans-4-propylcyclohexyl)ethyl]cyclohexanecarboxaldehyde.

Workup

  1. extractionextracted three times with 200 ml of diethyl ether each time
  2. washThe combined organic phases were washed first with saturated sodium hydrogen carbonate solution
  3. dry with materialwith water, dried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d590212cc2a348678932e23299701768
Source dataset
uspto-grants-1986_12
Patent number
US04630896

Reaction notes

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