3-Methylbutanal → 2-Methyloctan-4-ol

HRID 1197652Notes

Reaction equation

HRID 1197652 reaction equation
[CH:1](=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4].[CH2:7]([Mg]Cl)[CH2:8][CH2:9][CH3:10]>C1COCC1>[CH3:4][CH:3]([CH2:2][CH:1]([OH:6])[CH2:7][CH2:8][CH2:9][CH3:10])[CH3:5]

Participants

4

Procedure

A solution of isovaleraldehyde (5.o g, 58 mmol) in dry THF (15 ml) was added to a stirred 2M THF solution of n-butylmagnesium chloride (30 ml, 60 mmol) at 0° C. under argon. The mixture was allowed to warm up to room temperature and was stirred overnight. The reaction was quenched by the addition of aqueous ammonium chloride (50 ml) and extracted with diethyl ether (200 ml). The organic extracts were dried over anhydrous potassium carbonate, filtered and concentrated to give 2-methyloctan-4-ol (6.4 g, 77%) as a clear oil.

Workup

  1. customThe reaction was quenched by the addition of aqueous ammonium chloride (50 ml)
  2. extractionextracted with diethyl ether (200 ml)
  3. dry with materialThe organic extracts were dried over anhydrous potassium carbonate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c35b8c42b37c40a09abd1ddf2cb2a3a4
Source dataset
uspto-grants-1994_01
Patent number
US05276153

Reaction notes

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