Butyl bromide → 4-Methylnon-3-en-5-ol

HRID 1381078Notes

Reaction equation

HRID 1381078 reaction equation
[Mg].[CH2:2](Br)[CH2:3][CH2:4][CH3:5].[CH3:7][C:8](=[CH:11][CH2:12][CH3:13])[CH:9]=[O:10]>CCOCC>[CH3:7][C:8]([CH:9]([OH:10])[CH2:2][CH2:3][CH2:4][CH3:5])=[CH:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 121772-Methyl-2-pentenalHCID 5462224Magnesium

Product 1

HCID 538223604-Methylnon-3-en-5-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A Grignard reagent [29.1 g (1.2 g atoms) of magnesium in 300 ml of ether and 164 g (1.2 mol) of butyl bromide in 500 ml of ether] is reacted with 98.15 g (1 mol) of 2-methyl-2-pentenal in 200 ml of ether in a manner analogous to Example 5. Fractional distillation of the crude product (195.2 g) over a 20 cm Widmer column gives 124.2 g (79.5%) of olfactorily good 4-methyl-3-nonen-5-ol of boiling point 89°-90° C./12 mm Hg.

Workup

  1. distillationFractional distillation of the crude product (195.2 g) over a 20 cm Widmer column

Sources & evidence

ORD record
ord-52efca53216949b083b1a27f14d7c899
Source dataset
uspto-grants-1986_04
Patent number
US04585662

Reaction notes

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