Dimethyl Sulfate → 2-Methoxy-4-[(3-methyl-2-buten-1-yl)oxy]benzaldehyde

HRID 394961Notes

Reaction equation

HRID 394961 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].S(OC)(O[CH3:20])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:20][O:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 108674672-hydroxy-4-(3methylbut-2-enyloxy)benzaldehyde

Product 1

HCID 110853192-Methoxy-4-[(3-methyl-2-buten-1-yl)oxy]benzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

10.6 g (206 mmol) of 2-hydroxy-4-(3methylbut-2-enyloxy)benzaldehyde and 5.4 ml of dimethyl sulfate were dissolved in 102 ml of distilled acetone, the solution was added 25.5 g of potassium carbonate, and the resulting mixture was refluxed for 5 hours. The mixture was filtered and the filtrate concentrated in vacuo to give 8.3 g of an yellow oil from which 5.4 g of 2-methoxy-4-(3-methylbut-2-enyloxy)benzaldehyde was isolated by column chromatography over silica gel 60 (Merck 0.063-0.200 mm, 400 g) using petroleum ether-ethyl acetate (9:1, 1000 ml), (4:1, 500 ml) as eluents.

Workup

  1. temperaturethe resulting mixture was refluxed for 5 hours
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-8113b0065b294ab48b3e2ba2db66c478
Source dataset
uspto-grants-2003_08
Patent number
US06603046B1

Reaction notes

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