Water → 4-Methoxy-3-(3-methoxypropoxy)benzaldehyde

HRID 1690605Notes

Reaction equation

HRID 1690605 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].[CH3:12][O:13][CH2:14][CH2:15][CH2:16]Br.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C.C(OCC)(=O)C>[CH3:11][O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[O:1][CH2:16][CH2:15][CH2:14][O:13][CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12127IsovanillinHCID 5245511-Bromo-3-methoxypropane

Product 1

HCID 112183584-Methoxy-3-(3-methoxypropoxy)benzaldehydeYield 99.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-hydroxy-4-methoxybenzaldehyde (15 g, 98.6 mmol) was dissolved in acetonitrile (200 mL). 1-Methoxy-3-bromopropane (16.6 g, 108 mmol) and potassium carbonate (34 g, 247 mmol) were added and the mixture was brought to reflux and stirred for 3 hrs. After cooling to room temperature, water and ethyl acetate were added. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to yield 22 g (quantitative yield) of the desired product as a yellow oil, used without further purification.

Workup

  1. temperatureto reflux
  2. extractionThe aqueous layer was extracted three times with ethyl acetate
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-39c341f5ded94858a5f02a4f6d80ea2f
Source dataset
uspto-grants-2012_04
Patent number
US08153647B2

Reaction notes

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