Water → 3-(4-Pyridyloxy)-benzaldehyde dimethyl acetal

HRID 1740436Notes

Reaction equation

HRID 1740436 reaction equation
[CH3:1][O:2][CH:3]([O:11][CH3:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[CH:5]=1.CC(C)([O-])C.[K+].Cl.Cl[C:21]1[CH:26]=[CH:25][NH+:24]=[CH:23][CH:22]=1.O>CN(C)C=O>[CH3:1][O:2][CH:3]([O:11][CH3:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11275229Phenol, 3-(dimethoxymethyl)-HCID 221178644-Chloropyridinium hydrochlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 221178733-(4-Pyridyloxy)-benzaldehyde dimethyl acetal

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1 g of 3-hydroxybenzaldehyde dimethyl acetal and 2 g of potassium tert.butoxide in 10 ml of anhydrous dimethylformamide was heated at 60° C. under an atmosphere of dry nitrogen for 1 hour. The mixture was then cooled to room temperature and 900 mg of 4-chloropyridinium hydrochloride were added portionwise over a period of 20 minutes. The mixture was then heated at 160° C. for 18 hours, cooled, 100 ml of water were added and the product was extracted with ethyl acetate. The combined extracts were washed with 1M aqueous sodium hydroxide solution and with brine, and then dried over anhydrous magnesium sulphate. Evaporation to dryness left a brown oil which was purified by column chromatography on silica gel using hexane/ethyl acetate (gradient: 90:10 to 20:80) for the elution to give 3-(4-pyridyloxy)-benzaldehyde dimethyl acetal as a light brown oil.

Workup

  1. temperatureThe mixture was then heated at 160° C. for 18 hours
  2. temperaturecooled
  3. extractionthe product was extracted with ethyl acetate
  4. washThe combined extracts were washed with 1M aqueous sodium hydroxide solution and with brine
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customEvaporation to dryness
  7. waitleft a brown oil which
  8. customwas purified by column chromatography on silica gel
  9. washfor the elution

Sources & evidence

ORD record
ord-d1ac9ec4a5f641e2bed901653300194d
Source dataset
uspto-grants-1999_10
Patent number
US05969139

Reaction notes

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