Ammonium Chloride → 3-(trans-4-(trans-4-Propylcyclohexyl)cyclohexyl)propanol

HRID 386329Notes

Reaction equation

HRID 386329 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14]2)[CH2:9][CH2:8]1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>C1COCC1>[CH2:19]([CH:16]1[CH2:17][CH2:18][CH:13]([CH:10]2[CH2:11][CH2:12][CH:7]([CH2:6][CH2:5][CH2:4][OH:3])[CH2:8][CH2:9]2)[CH2:14][CH2:15]1)[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 592890743-(4'-Propyl-bicyclohexyl-4-yl)-propionic acid ethyl ester

Product 1

HCID 184179123-(trans-4-(trans-4-Propylcyclohexyl)cyclohexyl)propanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-(4′-Propyl-bicyclohexyl-4-yl)-propionic acid ethyl ester (22.0 g, 70 mmol) in THF (150 ml) is added dropwise to a suspension of lithium-aluminiumhydride (3.25 g, 86 mmol) in THF (250 ml) at reflux temperature. The reaction is heated under reflux for 1 h, cooled and poured onto sat. ammonium chloride solution. The mixture is acidified, extracted with ether and the combined organic layers are washed with brine and dried over sodium sulfate. The solvent is evaporated and the crude product is crystallised from isopropanol to give 3-(4′-propyl-bicyclohexyl-4-yl)-propan-1-ol as colourless crystals.

Workup

  1. temperatureat reflux temperature
  2. temperatureThe reaction is heated
  3. temperatureunder reflux for 1 h
  4. temperaturecooled
  5. extractionextracted with ether
  6. washthe combined organic layers are washed with brine
  7. dry with materialdried over sodium sulfate
  8. customThe solvent is evaporated
  9. customthe crude product is crystallised from isopropanol

Sources & evidence

ORD record
ord-a1f6099a371442c29f7e4c271bf169bf
Source dataset
uspto-grants-2013_02
Patent number
US08372307B2

Reaction notes

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