Hydrochloric Acid → HCID 22375161, compound

HRID 1956090Notes

Reaction equation

HRID 1956090 reaction equation
[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([CH:12]2[CH2:17][CH2:16][CH:15]([CH2:18]CCC=O)[CH2:14][CH2:13]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)(=O)C.Cl.[CH2:36]1C[O:39][CH2:38][CH2:37]1>>[CH2:1]([CH:6]1[CH2:7][CH2:8][CH:9]([CH:12]2[CH2:17][CH2:16][CH:15]([CH2:18][CH:38]([OH:39])[CH2:37][CH3:36])[CH2:14][CH2:13]2)[CH2:10][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 53909522HCID 53909522, compound

Product 1

HCID 22375161HCID 22375161, compoundYield 99%

Procedure

While keeping inside of a reaction system at a temperature of lower than 10° C., a solution of 5.0 g (16.3 mmol) of 4-(4-pentylcyclohexyl)-(oxobutyl)cyclohexane obtained in Example 1 and dissolved in 35 ml of THF was added dropwise to a mixture of 0.46 g (12.2 mmol) of LAH and 2.5 ml of THF and further stirred for 5 hours at a room temperature. Under cooled condition, 5 ml of ethyl acetate and then 100 ml of 6N hydrochloric acid were added to terminate the reaction. After extracted with 50 ml of ethyl acetate, the organic layer was washed with water twice and dried over anhydrous magnesium sulfate. After the magnesium sulfate was separated, the solvent was distilled off under a reduced pressure, and the residue thus obtained was recrystallized from 8 ml of hexane to obtain 5.0 g (yield 99%) of 4-(4-pentylcyclohexyl)-(2-hydroxybutyl)cyclohexane. Melting point: 130.9°-131.1° C.

Workup

  1. customlower than 10° C.
  2. customto terminate
  3. customthe reaction
  4. extractionAfter extracted with 50 ml of ethyl acetate
  5. washthe organic layer was washed with water twice
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter the magnesium sulfate was separated
  8. distillationthe solvent was distilled off under a reduced pressure
  9. customthe residue thus obtained
  10. customwas recrystallized from 8 ml of hexane

Sources & evidence

ORD record
ord-15712abbd7be46b98c1b9dec8ceb4e18
Source dataset
uspto-grants-1998_07
Patent number
US05779936

Reaction notes

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