Chloroform → 6-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

3.69 g of 6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one was dissolved in 70 ml of anhydrous methylene chloride. The obtained solution was cooled in a dry ice-acetone bath. Thereafter, 36 ml of boron tribromide (a 1.0 M methylene chloride solution) was added thereto, and the obtained mixture was stirred at room temperature overnight. Thereafter, the reaction solution was again cooled in a dry ice-acetone bath. 36 ml of boron tribromide (a 1.0 M methylene chloride solution) was added thereto, and the obtained mixture was stirred at room temperature overnight. Thereafter, the reaction solution was poured into ice, and chloroform was then added thereto. An insoluble precipitate was removed by filtration. The organic layer was separated and then dried over anhydrous sodium sulfate. The obtained solution was passed through a glass filter filled with silica gel, and the solvent was removed under a reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain 1.52 g of the subject compound.

1. temperatureThe obtained solution was cooled in a dry ice-acetone bath
2. temperatureThereafter, the reaction solution was again cooled in a dry ice-acetone bath
3. stirringthe obtained mixture was stirred at room temperature overnight
4. additionwas then added
5. customAn insoluble precipitate was removed by filtration
6. customThe organic layer was separated
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfilter
9. additionfilled with silica gel
10. customthe solvent was removed under a reduced pressure
11. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-489cfc6ed8544860b11d775795c09024

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07538123B2