1,5,9-Cyclododecatriene → Cyclododeca-1,3,5-triene

HRID 1413709Notes

Reaction equation

HRID 1413709 reaction equation
[CH:1]1[CH2:12][CH2:11][CH:10]=[CH:9][CH2:8][CH2:7][CH:6]=[CH:5][CH2:4][CH2:3][CH:2]=1.C(C1CCCCCCCCC=1)=O>>[CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:1][CH:2]=[CH:3][CH:4]=1

Participants

3

Reactant 2

HCID 126681,5,9-CyclododecatrieneHCID 54553785Formyl cyclodecene

Product 1

HCID 53421619Cyclododeca-1,3,5-triene

Procedure

The hydroformylation of cyclododeca-1,5,9-triene is known (U.S. Pat. Nos. 3,312,742 and 3,354,229; French Pat. No. 1,411,448 or British Pat. No. 1,161,147). According to these patents, corresponding C13 -alcohols and mixtures containing formyl cyclodocane in addition to formyl cyclodecene, formyl cyclodocadiene and the C13 -alcohol can be produced from cyclododecatriene using cobalt catalysts. Even under controlled conditions, the yield of formyl cyclododecane does not exceed 40% of the theoretical. Hydroxymethyl cyclododecanes are always obtained as the main product. Even under conditions under which formyl cyclooctane is obtained in a 56.7% yield from cycloocta-1,5-diene, hydroxymethyl cyclododecane is almost exclusively formed from cyclododeca-1,5,9-triene.

Workup

  1. additioncontaining formyl cyclodocane

Sources & evidence

ORD record
ord-5a4973ad187d46f1b1fba83ef574a0ba
Source dataset
uspto-grants-1981_02
Patent number
US04251462

Reaction notes

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