Cyclopentadiene → Bicyclo(2.2.1)hept-5-ene-2-carboxaldehyde

HRID 928893Notes

Reaction equation

[CH:1]([CH:3]=[CH2:4])=[O:2].[CH:5]1[CH2:9][CH:8]=[CH:7][CH:6]=1>>[CH:6]12[CH2:5][CH:9]([CH:3]([CH:1]=[O:2])[CH2:4]1)[CH:8]=[CH:7]2

Participants

Reactant 2

HCID 7612Cyclopentadiene

HCID 7847Acrolein

Product 1

HCID 95117Bicyclo(2.2.1)hept-5-ene-2-carboxaldehyde

Procedure

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.

Workup

customin a Diels-Alder reaction

Sources & evidence

ORD record: ord-eb6d558c50e149c9a2b7cd76f8959426
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290675B2

Reaction notes

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