Reaktion #347797

Reaktionsgleichung

2-methyl-1-naphthol

triethylamine

acetyl chloride

→

title compound

Ausbeute 63.1%

1-acetoxy-2-methylnaphthalene

Ausbeute 63.1%

Lösungsmittel

ethyl acetate

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedid not rise about 5° C
2. 2
   Waschenwashed with water
3. 3
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated
6. 6
   Sonstigeto give an oily residue
7. 7
   SonstigeCrystallization in hexane

Vorschrift

A solution of 9.48 g (60 mmole) of 2-methyl-1-naphthol and 8.10 g (80 mmole) of triethylamine in 50 mL of ethyl acetate was cooled to below 5° C. in an ice-bath. 5.50 g (70 mmole) of acetyl chloride was added at a rate such that the temperature did not rise about 5° C. The reaction mixture was stirred for an additional one hour, diluted with 50 mL of ethyl acetate, and washed with water then brine. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to give an oily residue. Crystallization in hexane yielded 7.58 g (63% yield) of the title compound with a melting point of 81°-83° C. and an 1HNMR as follows: (300 MHz, DMSO-d6) δ 2.26 ) (s, 3H), 2.48 (s, 3H), 7.42 (d, 1H, J=9 Hz), 7.46-7.55 (m, 2H), 7.47-7.81 (m, 2H), 7.92 (d, 1H, J=9 Hz). The mass spectrum showed a molecular ion at m/z 200.

Quelle