Aluminium lithium hydride → 2-(1-Methylcyclohexyl)ethanol

HRID 1806909Notes

Reaction equation

HRID 1806909 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1([CH3:11])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH3:11][C:5]1([CH2:4][CH2:3][OH:2])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67296891(1-Methyl-cyclohexyl)-acetic acid methyl ester

Product 1

HCID 2319302-(1-Methylcyclohexyl)ethanolYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Step C To a solution of (1-methyl-cyclohexyl)-acetic acid methyl ester (3.3 g, 19.4 mmol) in anhydrous tetrahydrofuran (50 mL) at 0° C. was added a tetrahydrofuran solution (1 M) of LiAlH4 (29 mL, 29 mmol) under nitrogen. The reaction mixture was stirred at 0° C. for 1 h, then poured into a ice-water. The mixture was extracted with ethyl acetate. The organic layer were separated, washed with water, aqueous HCl solution, brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:4) to give 2-(1-methyl-cyclohexyl)-ethanol as a colorless oil (2.2 g, 80%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. customThe organic layer were separated
  3. washwashed with water, aqueous HCl solution, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (EtOAc:hexanes=1:4)

Sources & evidence

ORD record
ord-381629be39f64f37912ea01ff6b2f4fc
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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