Hexamethylenetetramine → 4-Isopropyl salicylaldehyde

Temperature

60 °C

To 100 mL of trifluoroacetic acid were added 25.39 g of 3-isopropylphenol and 26.14 g of hexamethylenetetramine. After being stirred at 60° C. for an hour, the reaction mixture was concentrated under reduced pressure. To the residue was added diluted hydrochloric acid, and the mixture was stirred at room temperature for 30 minutes. After the reaction mixture was extracted with ethyl acetate, the organic layer was washed with saturated aqueous sodium bicarbonate solution, and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane) to give 6.69 g of 2-hydroxy-4-isopropylbenzaldehyde.

1. concentrationthe reaction mixture was concentrated under reduced pressure
2. additionTo the residue was added diluted hydrochloric acid
3. stirringthe mixture was stirred at room temperature for 30 minutes
4. extractionAfter the reaction mixture was extracted with ethyl acetate
5. washthe organic layer was washed with saturated aqueous sodium bicarbonate solution, and brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customThe solvent was removed under reduced pressure
8. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane)

ORD record

ord-06d97c7dbbd84e6babd8a7cc06b4928b

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07589126B2