Ethyl Acetate → HCID 22375212, compound

HRID 1956093Notes

Reaction equation

HRID 1956093 reaction equation
[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([CH:12]2[CH2:17][CH2:16][CH:15]([O:18][CH2:19][C:20](=[O:23])[CH2:21][CH3:22])[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(OC(=O)C)C>C1COCC1>[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([CH:12]2[CH2:13][CH2:14][CH:15]([O:18][CH2:19][CH:20]([OH:23])[CH2:21][CH3:22])[CH2:16][CH2:17]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 22375175HCID 22375175, compound

Product 1

HCID 22375212HCID 22375212, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

While keeping inside of a reaction system at a temperature of lower than 10° C., a solution of 5.24 g (16.3 mmol) of 4-(4-pentylcyclohexyl)-(2-oxobutyloxy)cyclohexane produced in Example 3 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. To this solution, under cooling, were added 5 ml of ethylacetate and then 10 ml of 2N aqueous solution of sodium hydroxide to terminate the reaction. After undissolved products were separated, the solvent was distilled off under a reduced pressure and the residue thus obtained was recrystallized from 15 ml of hexane to obtain 5.0 g (yield 95%) of 4-(4-pentylcyclohexyl)-(2-hydroxybutyloxy)cyclohexane.

Workup

  1. customlower than 10° C.
  2. temperatureTo this solution, under cooling
  3. custom10 ml of 2N aqueous solution of sodium hydroxide to terminate
  4. customthe reaction
  5. customAfter undissolved products were separated
  6. distillationthe solvent was distilled off under a reduced pressure
  7. customthe residue thus obtained
  8. customwas recrystallized from 15 ml of hexane

Sources & evidence

ORD record
ord-39bb056ebece4225996da48174a41ebd
Source dataset
uspto-grants-1998_07
Patent number
US05779936

Reaction notes

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