Ethylvanillin → 3-Ethoxy-4-(1-ethylpropoxy)benzaldehyde

HRID 547923Notes

Reaction equation

HRID 547923 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1C)[CH:7]=[O:8])[CH3:2].C([O:15][C:16]1[CH:17]=[C:18](C=[CH:22][C:23]=1O)C=O)C.BrC(CC)CC.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:15][CH:16]([CH2:17][CH3:18])[CH2:23][CH3:22])[CH:7]=[O:8])[CH3:2]

Participants

6

Reactant 4

HCID 8467EthylvanillinHCID 11430Potassium CarbonateHCID 157383-BromopentaneHCID 252420583-Ethoxy-4-methylbenzaldehyde

Product 1

HCID 591282713-Ethoxy-4-(1-ethylpropoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared analogously to 3-ethoxy-4-methyl-benzaldehyde (intermediate B21, vide infra) by reaction of 3-ethoxy-4-hydroxy-benzaldehyde with 3-bromo-pentane in DMF using K2CO3 as base. MS (ISP): 237.1 [M+H]+.

Sources & evidence

ORD record
ord-89861a375c494dc48fef37666ae9caf0
Source dataset
uspto-grants-2011_05
Patent number
US07939661B2

Reaction notes

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