Water → 3-(Cyclopropylmethoxy)-4-methoxybenzaldehyde

HRID 2230141Notes

Reaction equation

HRID 2230141 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].Br[CH2:13][CH:14]1[CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH:14]1([CH2:13][O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=2[O:10][CH3:11])[CH:5]=[O:6])[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12127IsovanillinHCID 81503Bromomethylcyclopropane

Product 1

HCID 222466233-(Cyclopropylmethoxy)-4-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-hydroxy-4-methoxybenzaldehyde (400 g, 2.63 mole) and bromomethylcyclopropane (426 g, 3.2 mole) in 1 L dimethylformamide (DMF) was stirred with potassium carbonate (K2CO3) (483 g, 3.5 mole) at 55° C. for 3.5 h. Then, 1 L of water was added, the mixture chilled on ice, and Intermediate 1 filtered as a white solid, (535 g, 99%). m/z 207 (MH+).

Workup

  1. filtrationfiltered as a white solid, (535 g, 99%)

Sources & evidence

ORD record
ord-44df9b972a5a4f34ba6e0fa92720c66a
Source dataset
uspto-grants-2002_07
Patent number
US06423710B1

Reaction notes

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