HCID 54447631, compound → 8,8-Diethoxy-3,7-dimethylocta-2,4,6-trienal

HRID 1729844Notes

Reaction equation

HRID 1729844 reaction equation
[CH2:1]([O:3][CH:4]([O:15][CH2:16][CH3:17])[C:5]([CH3:14])=[CH:6][CH:7]=[CH:8][C:9]([CH3:13])=[CH:10][CH2:11][OH:12])[CH3:2]>CCOCC>[CH2:16]([O:15][CH:4]([O:3][CH2:1][CH3:2])[C:5]([CH3:14])=[CH:6][CH:7]=[CH:8][C:9]([CH3:13])=[CH:10][CH:11]=[O:12])[CH3:17]

Participants

3

Reactant 1

HCID 54447631HCID 54447631, compound

Product 1

HCID 541827318,8-Diethoxy-3,7-dimethylocta-2,4,6-trienal

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

31.1 g. of 1,1-diethoxy-2,6-dimethyl-2,4,6-octatrien-8-ol are dissolved in a mixture of 800 ml. of petroleum ether (boiling range 40°-45° C.) and 200 ml. of ether, and after the addition of 150 g. of manganous oxide, shaken for 16 hours at room temperature. The mixture is then filtered, washed with ether, and after evaporation of the filtrate, 22 g. of 1,1-diethoxy-2,6-dimethyl-2,4,6-octatrien-8-al is obtained, which can be used for the Wittig reaction without further purification. The aldehyde can be purified through adsorption on aluminum oxide (activity II deactivated with 2 per cent water and 0.5 per cent pyridine). A small portion is removed by washing with a petroleum ether/ether mixture (95:5). By elution with a petroleum ether/ether mixture (3:1), there is obtained pure 1,1-diethoxy-2,6-dimethyl-2,4,6-octatrien-8-al (Abs. Max. 325 mμ; E11 = 1200; nD24 = 1.5607). Melting point of the di-semicarbazone 242°-243° C. with decomposition.

Workup

  1. filtrationThe mixture is then filtered
  2. washwashed with ether
  3. customafter evaporation of the filtrate, 22 g

Sources & evidence

ORD record
ord-595ad2522dcf489bb1bf6067de557477
Source dataset
uspto-grants-1976_11
Patent number
US03989758

Reaction notes

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