Hydrochloric Acid → 2-(2-Methylpropoxy)benzaldehyde

HRID 501782Notes

Reaction equation

HRID 501782 reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:17][C:18]([CH3:20])=[CH2:19].Cl>CN(C)C=O.O.C(OCC)(=O)C>[CH2:17]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH:1]=[O:9])[CH:18]([CH3:20])[CH3:19]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6998SalicylaldehydeHCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium Carbonate

Product 1

HCID 38575282-(2-Methylpropoxy)benzaldehyde

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

70.0 g of salicylaldehyde and 158.5 g of potassium carbonate were suspended in 700 mL of N,N-dimethylformamide, to which 68 mL of 3-chloro-2-methyl-1-propene was added dropwise over 30 minutes at 70° C., and this mixture was stirred for 30 minutes at the same temperature. Then, the reaction mixture was added to a mixture of ethyl acetate and water, and adjusted to pH 3 with 6M hydrochloric acid, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was dissolved in 350 mL of ethanol, to which 7.0 g of 5% palladium-carbon was added, and this mixture was stirred for 4 hours at 35° C. in a stream of hydrogen. After the reaction mixture was filtered through Celite, the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:toluene=2:1] to yield 92.4 g of 2-isobutoxybenzaldehyde as light yellow oil.

Workup

  1. additionwas added dropwise over 30 minutes at 70° C.
  2. customthe organic phase was separated
  3. washAfter the resultant organic phase was washed with water
  4. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled out under reduced pressure
  6. dissolutionThe resultant residue was dissolved in 350 mL of ethanol, to which 7.0 g of 5% palladium-carbon
  7. additionwas added
  8. stirringthis mixture was stirred for 4 hours at 35° C. in a stream of hydrogen
  9. filtrationAfter the reaction mixture was filtered through Celite
  10. distillationthe solvent was distilled out under reduced pressure
  11. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:toluene=2:1]

Sources & evidence

ORD record
ord-ff57cdcf4d0f4fc781a5f870bd63f80d
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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