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Dimethyl Sulfate → 3-ethoxy-2-methoxybenzaldehyde

HRID 1678595
Notes
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Reaction equation

HRID 1678595 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:6]([CH:7]=[O:8])[C:5]=1[OH:12])[CH3:2].[C:13](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4]1[C:5]([O:12][CH3:13])=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 68117O-Ethylvanillin

Product 1

HCID 24141193-ethoxy-2-methoxybenzaldehydeYield 101.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 3-ethoxysalicylaldehyde (1.00 g, 6.02 mmol) and potassium carbonate (3.33 g, 24.1 mmol) in N,N-dimethylformamide (10 mL) was added dimethyl sulfate (0.91 g, 7.22 mmol), and the mixture was stirred at 60° C. for 5 hours. The reaction mixture was diluted with ethyl acetate, filtered, and the filtrate was washed with water, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=7:3) to give the title compound (1.10 g, yield 99%) as an oily matter.

Workup

  1. filtrationfiltered
  2. washthe filtrate was washed with water
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=7:3)

Sources & evidence

ORD record
ord-c2db3961a91c4e36a95bf12787835c79
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08008525B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes