Hydrochloric Acid → 2-(4,4-Dimethylcyclohexyl)ethan-1-ol

HRID 397719

Reaction equation

HRID 397719 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:7][CH2:6][CH:5]([CH2:8][C:9](OCC)=[O:10])[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[CH3:1][C:2]1([CH3:14])[CH2:3][CH2:4][CH:5]([CH2:8][CH2:9][OH:10])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 23001036(4,4-Dimethyl-cyclohexyl)-acetic acid ethyl ester

Product 1

HCID 149767172-(4,4-Dimethylcyclohexyl)ethan-1-olYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(4,4-dimethylcyclohexyl)acetate (Preparation 14, 2.0 g, 10 mmol) in tetrahydrofuran (20 ml) under an atmosphere of nitrogen at 0° C. was added lithium aluminium hydride (1.0M solution in tetrahydrofuran, 11 ml, 11 mmol) and the reaction mixture was allowed to warm to room temperature overnight. The mixture was poured onto ice (300 g), acidified to pH 1 with 1N aqueous hydrochloric acid and extracted with dichloromethane (200 ml). The organic extract was dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as a pale yellow oil (1.45 g, 93%).

Workup

  1. additionThe mixture was poured onto ice (300 g)
  2. extractionextracted with dichloromethane (200 ml)
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60f7de8a69e34da7b1bc99c544292d17
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Linked notes

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