2-Methyl-2-pentenal → 4-Methyl-7-ethyl-3-nonen-5-ol

HRID 1381082Notes

Reaction equation

HRID 1381082 reaction equation
[Mg].Br[CH2:3][CH:4]([CH2:7][CH3:8])[CH2:5][CH3:6].[CH3:9][C:10](=[CH:13][CH2:14][CH3:15])[CH:11]=[O:12]>CCOCC>[CH3:9][C:10]([CH:11]([OH:12])[CH2:3][CH:4]([CH2:7][CH3:8])[CH2:5][CH3:6])=[CH:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 121772-Methyl-2-pentenalHCID 77432Pentane, 3-(bromomethyl)-HCID 5462224Magnesium

Product 1

HCID 538875094-Methyl-7-ethyl-3-nonen-5-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A Grignard reagent, prepared by reacting 11.4 g (0.47 g atom) of magnesium in 100 ml of ether and 77.6 g (0.47 mol) of 1-bromo-2-ethylbutane in 400 ml of ether, is reacted with 38.4 g (0.39 mol) of 2-methyl-2-pentenal in a manner analogous to Example 5. Fractional distillation of the crude product (79.8 g) over a 15 cm Widmer column gives 29.9 g (40.3%) of olfactorily good 4-methyl-7-ethyl-3-nonen-5-ol of boiling point 105°-106° C./12 mm Hg.

Workup

  1. distillationFractional distillation of the crude product (79.8 g) over a 15 cm Widmer column

Sources & evidence

ORD record
ord-4d7916ffd94d4fc19b2541f8398976c5
Source dataset
uspto-grants-1986_04
Patent number
US04585662

Reaction notes

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