Ethylvanillin → 3-Ethoxy-4-[(3-methylbut-2-en-1-yl)oxy]benzaldehyde

HRID 2264470Notes

Reaction equation

HRID 2264470 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[CH:7]=[O:8])[CH3:2].Br[CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17].C([O-])([O-])=O.[K+].[K+].C(OC1C=C(C=CC=1C)C=O)C>CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])[CH:7]=[O:8])[CH3:2]

Participants

6

Reactant 4

HCID 8467EthylvanillinHCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 252420583-Ethoxy-4-methylbenzaldehyde2×

Product 1

HCID 280656663-Ethoxy-4-[(3-methylbut-2-en-1-yl)oxy]benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared by reaction of 3-ethoxy-4-hydroxy-benzaldehyde with 1-bromo-3-methyl-2-butene in DMF using K2CO3 as base in analogy to the preparation of 3-ethoxy-4-methyl-benzaldehyde (intermediate D2).

Sources & evidence

ORD record
ord-77d3168e78c14da0a5ab2f79abb1bc66
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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