Sodium Hydroxide → Undeca-2,4,8-trienoic acid

HRID 724459Notes

Reaction equation

HRID 724459 reaction equation
[CH:1](=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH2:6][CH2:7][CH:8]=[CH:9][CH2:10][CH3:11].[OH-:13].[Na+]>O.[Ag-]=O>[C:1]([OH:13])(=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH2:6][CH2:7][CH:8]=[CH:9][CH2:10][CH3:11]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 71360942Undeca-2,4,8-trienal

Product 1

HCID 71418544Undeca-2,4,8-trienoic acid

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

cyclopentyl or allyl. The 2,4,8-undecatrienal is added to a suspension of silver (I) oxide (1.1 eq) in water. The mixture is stirred at 20° C. and 50% sodium hydroxide solution (equal weight to the aldehyde), is added over 30 minutes allowing the batch to exotherm to 60° C. The solution is filtered through celite, and the aqueous filtrate acidified to pH 1 with hydrochloric acid solution, to give 2,4,8-undecatrienoic acid.

Workup

  1. customto exotherm to 60° C
  2. filtrationThe solution is filtered through celite

Sources & evidence

ORD record
ord-7b79fda1377e41d9a31e57123bc49391
Source dataset
uspto-grants-2006_11
Patent number
US07141686B2

Reaction notes

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