Hexamethylenetetramine → 4'-Methyl-[1,1'-biphenyl]-4-carbaldehyde

温度

120 °C

Into CCl4 solvent, 2.4 g(13.3 mmol) of the compound produced in Example 1 (Compound 1) and 0.536 g(3.0 mmol) of N-bromosuccinimide were added and refluxed for 24 hours. After cooled down, the reactant was suction-filtrated and the resultant solution was washed with distilled water and then was dried with anhydrous magnesium sulfate. The dried product was dissolved again in chloroform together with 5.34 g(51.2 mmol) of hexamethylenetetraamine and refluxed for 5 hours. After the reactant was cooled down, the solvent was distilled off under reduced pressure and the residue was refluxed severely in acetic acid/H2O(17 mL/17 mL) at 120° C. for 2 hours. Finally, 7 mL of HCl was added to be refluxed. After cooled down, the reactant was extracted with methylene chloride. The solution was distilled off under reduced pressure and the residue was purified through the column chromatography (silica gel, ethyl acetate/n-hexane=1:3) to be dried. Yield; 24%.

1. temperaturerefluxed for 24 hours
2. temperatureAfter cooled down
3. filtrationthe reactant was suction-filtrated
4. washthe resultant solution was washed with distilled water
5. dry with materialwas dried with anhydrous magnesium sulfate
6. temperaturerefluxed for 5 hours
7. temperatureAfter the reactant was cooled down
8. distillationthe solvent was distilled off under reduced pressure
9. additionFinally, 7 mL of HCl was added
10. temperatureto be refluxed
11. temperatureAfter cooled down
12. extractionthe reactant was extracted with methylene chloride
13. distillationThe solution was distilled off under reduced pressure
14. customthe residue was purified through the column chromatography (silica gel, ethyl acetate/n-hexane=1:3)
15. customto be dried

ORDレコード

ord-f94605f221fa4e2ba1a3ca2ab5b8973f

出典データセット

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07592475B2