Allyl bromide → 3-Allyloxy-4-methoxybenzaldehyde

HRID 2243000Notes

Reaction equation

HRID 2243000 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(Br)C=C.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

6

Reactant 4

HCID 7841Allyl bromideHCID 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 D10) by reaction of 3-hydroxy-4-methoxy-benzaldehyde with allylbromide 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-8e1d6afb95624aac8d93114c612b7de3
Source dataset
uspto-grants-2010_03
Patent number
US07674804B2

Reaction notes

Loading…