Acetaldehyde → Cinnamaldehyde

HRID 2201610Notes

Reaction equation

[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:9](=[O:11])[CH3:10]>>[CH:5]1[CH:6]=[CH:7][C:2](/[CH:1]=[CH:10]/[CH:9]=[O:11])=[CH:3][CH:4]=1

Participants

Reactant 2

HCID 177Acetaldehyde

HCID 240Benzaldehyde

Product 1

HCID 637511Cinnamaldehyde

Procedure

As shown in Scheme 1, benzaldehyde derivative 1-1 can be reacted with acetaldehyde in the presence of either an acid or a base catalyst to afford cinnamic aldehyde 1-2. Reaction of cinnamic aldehyde 1-2 with an organometallic compound such as a Grignard reagent R8MgX1 [wherein X1 is halo such as Cl or Br], followed by oxidation of the intermediate alcohol to ketone and by reduction of the C═C bond to a C—C single bond under a hydrogenation condition (for example, in the presence of Pd/C catalyst), affords ketone 1-3. Reaction of ketone 1-3 with amine 1-4 under reductive amination condition (such as in the presence of a borohydride reducing reagent) affords compound 1-5.

Sources & evidence

ORD record: ord-c3d42e95e10640a387f90f407a83cc48
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365491B2

Reaction notes

Loading…