104093-22-3 → 5,5-dimethylhexan-1-ol

HRID 1737155Notes

Reaction equation

HRID 1737155 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

HCID 15760605104093-22-3HCID 21226445Aluminium lithium hydride

Product 1

HCID 2628495,5-dimethylhexan-1-olYield 77.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. custombefore quenching with 2 ml 15% NaOH and 6 ml water
  2. additionbefore diluting with dichloromethane
  3. filtrationfiltering through CELITE (RTM)
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-ad78d1dda0d14165b206a15060df0477
Source dataset
uspto-grants-1999_10
Patent number
US05962002

Reaction notes

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