Ethyl 5,5-dimethylhexanoate → 5,5-dimethylhexan-1-ol
Reaction equation
[CH3:1][C:2]([CH3:12])([CH3:11])[CH2:3][CH2:4][CH2:5][C:6](OCC)=[O:7].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][C:2]([CH3:12])([CH3:11])[CH2:3][CH2:4][CH2:5][CH2:6][OH:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Ethyl 5,5-dimethylhexanoate (1.87 g) (prepared in Example 34 with esterification), was dissolved in 30 ml of THF and lithium aluminium hydride (2 g) added portionwise. The reaction was stirred for 2 hours at 0° C. before quenching with 2 ml 15% NaOH and 6 ml water before diluting with dichloromethane and filtering through CELITE (RTM) and the solvent evaporated to give 5,5-dimethylhexanol product (1.1 g) as a slightly volatile liquid. This alcohol was dissolved in 30 ml dichloromethane containing pyridinium chlorochromate and stirred at room temperature to convert it to the corresponding aldehyde, 5,5-dimethylhexanal.