Butyl bromide → 3-Butoxy-4-methoxybenzaldehyde

HRID 2426579Notes

Reaction equation

HRID 2426579 reaction equation
C(O[C:4]1[CH:5]=C(C=[CH:10][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].BrCCCC.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])[CH2:4][CH2:11][CH3:10]

Participants

6

Reactant 4

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 12127IsovanillinHCID 252420583-Ethoxy-4-methylbenzaldehyde2×

Product 1

HCID 5924713-Butoxy-4-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared analogously to 3-ethoxy-4-methyl-benzaldehyde (intermediate D10, vide infra) by reaction of 3-hydroxy-4-methoxy-benzaldehyde with 4-bromo-butane in DMF using K2CO3 as base. MS (ISP): 209.1 [M+H]+.

Sources & evidence

ORD record
ord-56cd763eb9d04b6ead1c5b6d8b3c96b8
Source dataset
uspto-grants-2011_06
Patent number
US07968568B2

Reaction notes

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