ChemicalBook CAS DataBase List 6-(tert-Butyl)naphthalen-2-ol

6-(tert-Butyl)naphthalen-2-ol synthesis

7synthesis methods

Product Name:6-(tert-Butyl)naphthalen-2-ol
CAS Number:1081-32-9
Molecular formula:C14H16O
Molecular Weight:200.28

507-20-0 Synthesis

507-20-0
389 suppliers
$13.00/25mL

135-19-3 Synthesis

135-19-3
760 suppliers
$9.00/1g

1081-32-9
7 suppliers
inquiry

Yield: 12%

Reaction Conditions:

with aluminum (III) chloride in dichloromethane at 40; for 6 h;Inert atmosphere;

Steps:

4 Synthesis of Intermediate 4-2
In 150 ml of anhydrous dichioromethane, 34.9 g (242 mmol) of 2-naphthol, 47.3 g (510 mmol) of 2-chloro-2-methylpropane, and 2.45 g (18.4 mmol) of aluminium chloride were added in a nitrogen atmosphere. The resulting mixture was stirred for 6 hours at 40 degrees Celsius. After the reaction was completed, the mixture was cooled to a room temperature, and the solvent was distilled off under reduced pressure. In the resulting solution, 300 ml of 5% aqueous sodium hydroxide solution was added. The resulting mixture was stirred for 2 hours at 80 degrees Celsius and then filtered to separate a crystal. The crystal was then dissolved in 500 ml of chloroform, and 50 ml of hydrochloric acid was added dropwise into the solution. The resulting mixture was stilTed for 1 hour at a room temperature. Then, water was added in the mixture. The organic layer was extracted with chloroform and dried with anhydrous sodium sulfate. Subsequently, the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (gel used in chromatography: BW300 (produced by Fuji Silysia Chemical Ltd.), developing solvent: ethyl acetate/chloroform = 1/1). Thus, 5.9 g (yield 12%) of Compound 4-2 was prepared.

References:

CANON KABUSHIKI KAISHA;ABE, Shigemoto;KAMATANI, Jun;KISHINO, Kengo;SAITOH, Akihito;YAMADA, Naoki;KOSUGE, Tetsuya;HORIUCHI, Takayuki;NISHIDE, Yosuke;MIYASHITA, Hirokazu WO2014/115528, 2014, A1 Location in patent:Paragraph 0248; 0250