Sodium Chloride → 7-Hydroxy-2,3-dihydro-1H-inden-1-one

Temperature

50 °C

37.0 g (278 mmol) of aluminum chloride was mixed with 3.70 g (61.3 mmol) of sodium chloride, the mixture was dissolved at 150° C. under heating, 6.40 g (43.2 mmol) of commercially available 2,3-dihydro-4H-chromen-4-one dissolved by heating (50° C.) was added to the mixture and the resulting mixture was stirred at 200° C. for 20 minutes. The reaction mixture (gum state) was cooled, and added to ice-cold hydrochloric acid (100 ml of conc. hydrochloric acid and ice were combined to make them 200 ml) little by little and stirred for 30 minutes. Methylene chloride was added to the mixture and the mixture was separated. The aqueous layer was filtered, and the filtrate was extracted with methylene chloride. The organic layers were combined, washed successively with water and brine, and dried over sodium sulfate. The solvent was removed, and the obtained residue was purified by silica gel chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to obtain 4.82 g (32.6 mmol, Yield: 75.2%) of 7-hydroxy-1-indanone.

1. dissolutionthe mixture was dissolved at 150° C.
2. temperatureunder heating
3. additionwas added to the mixture
4. temperatureThe reaction mixture (gum state) was cooled
5. stirringstirred for 30 minutes
6. customthe mixture was separated
7. filtrationThe aqueous layer was filtered
8. extractionthe filtrate was extracted with methylene chloride
9. washwashed successively with water and brine
10. dry with materialdried over sodium sulfate
11. customThe solvent was removed
12. customthe obtained residue was purified by silica gel chromatography (Wakogel C-100, hexane-ethyl acetate, gradient)

ORD record

ord-ca2ba00f6ef1438ca45e14d88ed8d312

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07608563B2