Реакция #1090302

Уравнение реакции

diethylether

triethylamine

2-methyl-1-naphthol

methyl chloroformate

→

oil

Выход 85.0%

2-methyl-1-naphthalenol methylcarbonate

Выход 85.0%

Растворители

ethyl acetate

Условия реакции

Обработка

1. 1
   Температураwas maintained in an ice bath
2. 2
   ФильтрацияThe reaction mixture was filtered over a Celite pad
3. 3
   Концентрированиеthe filtrate concentrated

Методика

2.64 g (26 mmole) of triethylamine were added to a stirred solution of 3.16 g (20 mmole) of 2-methyl-1-naphthol in 25 mL of ethyl acetate, while the solution was maintained in an ice bath. Then 2.36 g (25 mmole) methyl chloroformate were added portionwise to the solution. The reaction mixture was stirred for one hour and then 100 mL diethylether was added. The reaction mixture was filtered over a Celite pad and the filtrate concentrated to give 3.65 g (85% yield) of an oil which was crystallized in hexane. The resulting crystals had a melting point of 54-55° C. The following 1HNMR was obtained: (300 MHz, DMSO-d6) δ2.30 (s, 3H), 3.89 (s, 3H), 7.44 (d, 1H, J=8 Hz), 7.48-7.58 (m, 2H), 7.78 (t, 2H, J=9 Hz), 7.95 (d, 1H, J=8 Hz). The mass spectrum showed a molecular ion at m/z 216.

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