Furfural → 3,7-Dimethylocta-2,6-Dienal

HRID 973190Notes

Reaction equation

HRID 973190 reaction equation
C([Al](CC(C)C)CC(C)C)C(C)C.[OH:14][CH2:15]/[CH:16]=[C:17](/[CH3:24])\[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22].C(=O)C1OC=CC=1>C1(C)C=CC=CC=1>[CH3:23][C:21](=[CH:20][CH2:19][CH2:18][C:17](=[CH:16][CH:15]=[O:14])[CH3:24])[CH3:22]

Participants

5

Reactant 3

HCID 7362FurfuralHCID 643820Nerol2×HCID 16682931Triisobutylaluminum2×

Product 1

HCID 88433,7-Dimethylocta-2,6-Dienal

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

This example illustrates the use of triisobutylaluminum to generate the aluminum alkoxide catalyst. A flask was charged with 80 grams of nerol and 10 ml of a 25% solution of triisobutylaluminum in toluene. To the solution was added 39 grams (0.75 equivalents) of furfural and the solution was allowed to react at ambient temperature for 18 hours. Analysis by glpc showed that 69% of the nerol had been consumed to give citral in 98+% yield.

Workup

  1. customto react at ambient temperature for 18 hours
  2. customhad been consumed

Sources & evidence

ORD record
ord-c20901e91e0b4c9e98dfefd9222db60f
Source dataset
uspto-grants-1977_10
Patent number
US04055601

Reaction notes

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