1,3-Butadiene → 1,4,8-Cyclododecatriene

HRID 338052

Reaction equation

HRID 338052 reaction equation
[CH:1]12[CH2:9][CH:4]([CH:5]([CH:7]=O)[CH2:6]1)[CH:3]=[CH:2]2.[CH:10]([CH:12]1CCC[CH:14](CCC=O)[CH2:13]1)=O.C(C1CCC(CCC=O)CC1)=O.C(C1CCCC(C(C)C=O)C1)=O.C(C1CCC(C(C)C=O)CC1)=O.C(C1CCCCC=1)=C.C1(C=O)CCCCC(C=O)CCCC(C=O)CC1.C=CC=C>>[CH:2]1[CH2:3][CH2:4][CH2:9][CH:1]=[CH:6][CH2:5][CH2:7][CH:10]=[CH:12][CH2:13][CH:14]=1

Participants

9

Reactant 8

HCID 78451,3-ButadieneHCID 17497VinylcyclohexeneHCID 95117Bicyclo(2.2.1)hept-5-ene-2-carboxaldehydeHCID 211920202-(3-Formylcyclohexyl)propanalHCID 211920232-(4-Formylcyclohexyl)propanalHCID 211920383-(3-Formylcyclohexyl)propanalHCID 211920393-(4-Formylcyclohexyl)propanalHCID 85667841Cyclododecane-1,4,8-tricarbaldehyde

Product 1

HCID 336861,4,8-Cyclododecatriene

Procedure

Examples of suitable cyclic polyaldehydes are trans-1,3-cyclohexanedicarboxaldehyde; cis-1,3-cyclohexanedicarboxaldehyde; trans-1,4-cyclohexanedicarboxaldehyde; cis-1,4-cyclohexanedicarboxaldehyde; a mixture of 1,3-cyclohexanedicarboxaldehydes and 1,4-cyclohexanedicarboxaldehydes, preferably a 1-to-1 mixture thereof; exo,exo-2,5-norbornanedicarboxaldehyde; exo,exo-2,6-norbornanedicarboxaldehyde; exo,endo-2,5-norbornanedicarboxaldehyde; exo,endo-2,6-norbornanedicarboxaldehyde; endo,endo-2,5-norbornanedicarboxaldehyde; endo,endo-2,6-norbornanedicarboxaldehyde product (endo and exo mixture); 3-(3-formylcyclohexyl)propanal; 3-(4-formylcyclohexyl)propanal; 2-(3-formylcyclohexyl)propanal; 2-(4-formylcyclohexyl)propanal; and cyclododecane-1,4,8-tricarbaldehyde. The trans-1,3-cyclohexanedicarboxaldehyde; cis-1,3-cyclohexanedicarboxaldehyde; trans-1,4-cyclohexanedicarboxaldehyde; and cis-1,4-cyclohexanedicarboxaldehyde can be prepared by a process comprising hydroformylating 3-cyclohexene-1-carboxaldehyde using the hydroformylating conditions described later. The 1:1 mixture of 1,3- and 1,4-cyclohexanedicarboxaldehydes can be prepared by a process comprising reacting acrolein and 1,3-butadiene in a Diels-Alder reaction to give 3-cyclohexenecarboxaldehyde (also called 1,2,3,6-tetrahydrobenzaldehyde), and hydroformylating the 3-cyclohexenecarboxaldehyde. The exo,exo-2,5-norbornanedicarboxaldehyde; exo,exo-2,6-norbornanedicarboxaldehyde; exo,endo-2,5-norbornanedicarboxaldehyde; exo,endo-2,6-norbornanedicarboxaldehyde; endo,endo-2,5-norbornanedicarboxaldehyde; and endo,endo-2,6-norbornanedicarboxaldehyde product (endo and exo mixture) can be prepared by a process comprising reacting acrolein and cyclopentadiene in a Diels-Alder reaction to give a 2-norbornene-5-carboxaldehyde, and hydroformylating the 2-norbornene-5-carboxaldehyde. The 3-(3-formylcyclohexyl)propanal; 3-(4-formylcyclohexyl)propanal; 2-(3-formylcyclohexyl)propanal; and 2-(4-formylcyclohexyl)propanal can be prepared by a process comprising hydroformylating vinyl cyclohexene. The cyclododecane-1,4,8-tricarbaldehyde can be prepared by a process comprising trimerizing 1,3-butadiene to give 1,4,8-cyclododecatriene, and hydroformylating the 1,4,8-cyclododecatriene.

Sources & evidence

ORD record
ord-d41d798e2a794f4bad26dbde4057a92f
Source dataset
uspto-grants-2014_11
Patent number
US08889818B2

Linked notes

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