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

HRID 1990814Notes

Reaction equation

HRID 1990814 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+]>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

5

Reactant 3

HCID 8467EthylvanillinHCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-

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 analogously to intermediate 2 (4-methoxy-3-propoxy-benzaldehyde) by reaction of 3-ethoxy-4-hydroxy-benzaldehyde with 1-bromo-3-methyl-2-butene in DMF using K2CO3 as base. MS (ISN): 233.1 [M−H]−.

Sources & evidence

ORD record
ord-38fce737d636413eb36aae3b19c280d6
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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