Ammonium Chloride → HCID 59289064, compound

HRID 386339Notes

Reaction equation

HRID 386339 reaction equation
C([O:3][C:4](=O)[CH:5]([CH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH3:17])[CH2:11][CH2:10]1)[CH2:6][CH3:7])C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>C1COCC1>[CH2:15]([CH:12]1[CH2:11][CH2:10][CH:9]([CH2:8][CH:5]([CH2:6][CH3:7])[CH2:4][OH:3])[CH2:14][CH2:13]1)[CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 59289087HCID 59289087, compound

Product 1

HCID 59289064HCID 59289064, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(4-propyl-cyclohexylmethyl)-butyric acid ethyl ester (35.0 g, 138 mmol) in THF (300 ml) is added dropwise to a suspension of lithium-aluminiumhydride (6 g, 158 mmol) in THF (300 ml) at reflux temperature. The reaction mixture 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 2-(4-propyl-cyclohexylmethyl)-butan-1-ol as colourless crystals.

Workup

  1. temperatureat reflux temperature
  2. temperatureThe reaction mixture 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-94412ceaaa2848dbb5cad0e7f7046edb
Source dataset
uspto-grants-2013_02
Patent number
US08372307B2

Reaction notes

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