Hydrochloric Acid → 5-Methoxy-2-(3-methylbut-2-enyloxy)benzaldehyde

HRID 30093

Reaction equation

HRID 30093 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22].Cl>CN(C)C=O.C(OCC)(=O)C>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:2]([O:1][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])=[C:3]([CH:6]=1)[CH:4]=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 956952-Hydroxy-5-methoxybenzaldehyde

Product 1

HCID 105849975-Methoxy-2-(3-methylbut-2-enyloxy)benzaldehyde

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-hydroxy-5-methoxybenzaldehyde (7.6 g, 50 mmol) in dry N,N-dimethylformamide (100 mL) was added potassium carbonate (10.4 g), followed by 1-bromo-3-methylbut-2-ene (10.0 g, 67 mmol). The mixture was stirred at room temperature for 48 hours and ethyl acetate added. Sufficient 1M hydrochloric acid was cautiously added to neutralize the base, and the organic layer was washed with water three times, followed by brine, and dried over magnesium sulfate. The mixture was filtered, and solvent removed from the filtrate under reduced pressure, to provide 5-methoxy-2-(3 -methylbut-2-enyloxy)benzaldehyde.

Workup

  1. washthe organic layer was washed with water three times
  2. dry with materialdried over magnesium sulfate
  3. filtrationThe mixture was filtered
  4. customsolvent removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-06f988e364c540fbacba7f1878f5c21d
Source dataset
uspto-grants-2008_09
Patent number
US07423045B2

Linked notes

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