4-Hydroxybenzaldehyde → HCID 21084478, compound

In methanol, 4-hydroxybenzaldehyde (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (1.00 g) was dissolved. Then, the solution was added with dipropylamine (1.24 ml), trimethyl orthoformate (1.0 ml), and acetic acid (500 μl) and stirred at room temperature for 15 minutes. The solution was cooled to 0° C. and added with sodium cyanoborohydride (773 mg), followed by stirring for 6 hours at room temperature. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was then dissolved in chloroform, followed by the addition of water. The solution was adjusted to about pH 7 with a 1 mol/l sodium hydroxide aqueous solution and then subjected to extraction with chloroform. The resulting organic layer was washed with saturated saline solution and then dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue was then purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (76.8 mg) as a pale-yellow solid.

1. temperatureThe solution was cooled to 0° C.
2. stirringby stirring for 6 hours at room temperature
3. customAfter completion of the reaction
4. distillationthe solvent was distilled off under reduced pressure
5. dissolutionthe residue was then dissolved in chloroform
6. additionfollowed by the addition of water
7. extractionsubjected to extraction with chloroform
8. washThe resulting organic layer was washed with saturated saline solution
9. dry with materialdried with anhydrous sodium sulfate
10. filtrationAfter filtration
11. distillationthe solvent was distilled off under reduced pressure
12. customthe residue was then purified through silica gel column chromatography (chloroform/methanol)

ORD record

ord-976ba7fa002e4b37a59f903877cbd0ee

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07176227B2