Potassium Carbonate → 3-Allyloxy-4-methoxybenzaldehyde

HRID 2355596Notes

Reaction equation

HRID 2355596 reaction equation
C(O[C:4]1[CH:5]=C(C=C[C:11]=1C)C=O)C.[OH:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH:17]=[O:18].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:5]([O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH:17]=[O:18])[CH:4]=[CH2:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12127IsovanillinHCID 252420583-Ethoxy-4-methylbenzaldehyde

Product 1

HCID 5341483-Allyloxy-4-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared analogously to 3-ethoxy-4-methyl-benzaldehyde (intermediate E10) by reaction of 3-hydroxy-4-methoxy-benzaldehyde with alkylbromide in DMF using K2CO3 as base (see also A. W. White, R. Almassy, A. H. Calvert, N. J. Curtin, R. J. Griffin, Z. Hostomsky, K. Maegley, D. R. Newell, S. Srinivasan and B. T. Golding J. Med. Chem. 2000, 43, 4084-4097).

Sources & evidence

ORD record
ord-17976b1e76b34c91851186eaaf652455
Source dataset
uspto-grants-2010_07
Patent number
US07754744B2

Reaction notes

Loading…