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

HRID 2113549Notes

Reaction equation

HRID 2113549 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 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 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-44283678dccd44feb4b01f19ab857d96
Source dataset
uspto-grants-2008_10
Patent number
US07432276B2

Reaction notes

Loading…