Hydrochloric Acid → 3-(4-Acetoxybutoxy)-5-hydroxybenzaldehyde

HRID 1985823Notes

Reaction equation

HRID 1985823 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:10])[CH:9]=1)[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].[C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24]Br)(=[O:19])[CH3:18].Cl>CN(C)C=O>[C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:10])[CH:9]=1)[CH:5]=[O:6])(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 784911-Butanol, 4-bromo-, 1-acetateHCID 943653,5-Dihydroxybenzaldehyde

Product 1

HCID 231438823-(4-Acetoxybutoxy)-5-hydroxybenzaldehydeYield 32.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,5-Dihydroxybenzaldehyde (0.96 g) and potassium carbonate (1.44 g) were suspended in N,N-dimethylformamide (5 mL). To the mixture was added 4-bromobutyl acetate (1.49 g) under ice-cooling, and the mixture was stirred at room temperature for 16 hours. To the reaction mixture was added 1 mol/L hydrochloric acid, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine successively and dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/5) to give the title compound (0.57 g).

Workup

  1. temperaturecooling
  2. extractionthe resulting mixture was extracted with diethyl ether
  3. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe obtained residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/5)

Sources & evidence

ORD record
ord-589be94f517b4c5b9467395164e3d3af
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

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