Sodium Hydroxide → HCID 178448052, compound

HRID 989582Notes

Reaction equation

HRID 989582 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([CH2:16][CH2:17][CH:18]=[O:19])[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([CH2:16][CH2:17][CH2:18][OH:19])[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178448051HCID 178448051, compound

Product 1

HCID 178448052HCID 178448052, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

Under nitrogen gas stream, a solution of 400 g (1510 mmol) of the crude 3-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)propanal obtained in the same manner as in the third step in Example 1 in 2.0 l of THF was added by drops to a mixture which was prepared by adding 43.0 g (1130 mmol) of lithium aluminum hydride to 400 ml of THF cooled down to a temperature lower than 5° C., while being maintained at the same temperature. After finishing of the adding, they were stirred at room temperature for 6 hours. This reaction mixture was gradually added to 500 ml of 2N aqueous sodium hydroxide solution and stirred at 50° C. for 30 minutes. The reaction mixture was filtered with Celite, the solvent was distilled off under a reduced pressure, and the residue was extracted with 2.0 l of ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under a reduced pressure to obtain 341 g of a crude 3-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)propanol.

Workup

  1. additionwas added by drops to a mixture which
  2. customwas prepared
  3. temperaturewhile being maintained at the same temperature
  4. stirringstirred at 50° C. for 30 minutes
  5. filtrationThe reaction mixture was filtered with Celite
  6. distillationthe solvent was distilled off under a reduced pressure
  7. extractionthe residue was extracted with 2.0 l of ethyl acetate
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-7e7a6f579a1a4ab4952ea1303cee4741
Source dataset
uspto-grants-2002_10
Patent number
US06458433B1

Reaction notes

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