Diethylether water → 3,4,7-Trimethylnona-2,6-dien-1-ol

HRID 1112231Notes

Reaction equation

HRID 1112231 reaction equation
[CH3:1][C:2]([CH:10]([CH3:17])[CH2:11][CH:12]=[C:13]([CH3:16])[CH2:14][CH3:15])=[CH:3][CH2:4]C(OCC)=O.[H-].C[O:20]CCO[Al+]OCCOC.[Na+].[H-].O.CCOCC>C1C=CC=CC=1>[CH3:1][C:2]([CH:10]([CH3:17])[CH2:11][CH:12]=[C:13]([CH3:16])[CH2:14][CH3:15])=[CH:3][CH2:4][OH:20]

Participants

5

Reactant 3

HCID 21584184Diethylether waterHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 53646416HCID 53646416, compound

Product 1

HCID 540635383,4,7-Trimethylnona-2,6-dien-1-ol

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
40 °C

Procedure

157 g. of ethyl 3,4,7-trimethyl-2,6-nonadienecarboxylate are dissolved in 300 ml. of benzene and added dropwise while cooling with ice to a solution of 370 g. of 70% sodium bis-(methoxyethoxy)-aluminum hydride in benzene. The mixture is then stirred at 40° C. for 2 hours and subsequently worked up with water/ether as described earlier. The 3,4,7-trimethyl-2,6-nonadien-1-ol obtained boils at 79°-84° C./0.09 mmHg.

Workup

  1. temperaturewhile cooling with ice to a solution of 370 g

Sources & evidence

ORD record
ord-09e45984bda641b586bf46b9cd554a6e
Source dataset
uspto-grants-1978_10
Patent number
US04120974

Reaction notes

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