ChemicalBook CAS DataBase List 1-Acetoxy-2-met hoxynaphthalene

1-Acetoxy-2-met hoxynaphthalene synthesis

7synthesis methods

Product Name:1-Acetoxy-2-met hoxynaphthalene
CAS Number:5697-02-9
Molecular formula:C13H12O2
Molecular Weight:200.23

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75-36-5 Synthesis

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Yield: 63%

Reaction Conditions:

with triethylamine in ethyl acetate

Steps:

6 Preparation of 1-acetoxy-2-methylnaphthalene.
STR11 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 ¹ H-NMR 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.

References:

Clairol Incorporated US5529583, 1996, A