Hydrochloric Acid → Phlorisobutyrophenone

In a vessel fitted with a calcium chloride tube, 12.61 g (100.0 mmol) of 1,3,5-trihydroxybenzene (1) was suspended on a mixture of 35 ml of nitrobenzene and 45 ml of carbon disulfide and they were stirred. To the mixture, 40.0 g (300 mmol, 3.00 equivalents) of granular aluminum chloride was added piecemeal at room temperature. They were stirred for one hour and a nitrobenzene (10.0 ml) solution of 10.66 g (100.0 mmol, 1.000 equivalent) of isobutyryl chloride was slowly added dropwise to the mixture. After about 5 hours, the reaction mixture was poured into a cold 2 M hydrochloric acid (500 ml) solution to induce decomposition of aluminum salt and then was extracted from ether. The organic layer was washed with water and distilled off ether under a reduced pressure. To this was added a large amount of water and water was distilled under reduced pressure to remove nitrobenzene solvent by steam distillation method. The residue was dissolved in ether, washed with saturated brine, dried over sodium sulfate, and distilled under a reduced pressure to remove the solvent and obtain 21.7 g of a crude reaction product. By recrystallization of the crude product from petroleum ether-methylene chloride (1:1), 17.1 g (yield 87.2%) of the product (4) was obtained in the form of light yellow powdery crystals.

1. customIn a vessel fitted with a calcium chloride tube
2. stirringThey were stirred for one hour
3. extractionwas extracted from ether
4. washThe organic layer was washed with water
5. distillationdistilled off ether under a reduced pressure
6. additionTo this was added a large amount of water and water
7. distillationwas distilled under reduced pressure
8. customto remove nitrobenzene solvent
9. distillationby steam distillation method
10. dissolutionThe residue was dissolved in ether
11. washwashed with saturated brine
12. dry with materialdried over sodium sulfate
13. distillationdistilled under a reduced pressure
14. customto remove the solvent
15. customobtain 21.7 g of a crude
16. customreaction product
17. customBy recrystallization of the crude product from petroleum ether-methylene chloride (1:1)

ORD record

ord-5a7954490de54b9f94e4b416ea165a95

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06177474B1