6-methoxy-1-tetralone

Chemical properties

yellow to light brown fine crystalline powder

The Uses of 6-methoxy-1-tetralone

6-Methoxy-1-tetralone is a reagent useful in the synthesis of (2-(furanyl)vinyl)-1-tetralone chalcones which possesses anticancer agents and inducers of apoptosis.

Definition

ChEBI: 6-Methoxy-1-tetralone is a member of tetralins.

Preparation

(1) Reacting anisole with an acylating agent in Lewis acid and a solvent at the temperature of-10-40 ℃ to generate an intermediate 1, wherein the molar ratio of the Lewis acid to the acylating agent to the anisole is 1-10: 1-10: 1, the Lewis acid is selected from one or more of concentrated sulfuric acid, phosphoric acid, polyphosphoric acid, zinc chloride, aluminum trichloride, superacid and heteropoly acid;
(2) the intermediate 1 does not need to be separated, the temperature is raised to 70-120 ℃, and the intermediate 1 continues to react to generate 6-methoxy-1-tetralone;
(3) cooling the reaction product, adding water to stop the reaction, extracting, purifying and desolventizing to obtain a crude product of the 6-methoxy-1-tetralone, and refining the crude product by a solvent to obtain a high-purity product.

Synthesis Reference(s)

Journal of the American Chemical Society, 64, p. 94, 1942 DOI: 10.1021/ja01253a025
Tetrahedron Letters, 9, p. 2917, 1968 DOI: 10.1016/S0040-4039(00)89611-2

Synthesis

The synthesis of 6-methoxy-1-tetralone is as follows:Eaton's reagent (1.00 mL, 5.31 mmol) was added slowly to a stirred solution of methyl 4-(3-methoxyphenyl)butanoate (4; 0.37g, 1.78 mmol) in DCE (1 mL). The resulting mixture was stirred at 75 °C for 2h under N₂ atmosphere. Then, the reaction mixture was allowed to reach room temperature, and was poured over ice-water and extracted with EtOAc (3 × 15 mL). The combined organic extracts were washed successively with brine (2 × 15 mL) and H₂O (2 × 20 mL), filtered over Na₂SO₄ and concentrated under reduced pressure. The resulting brownish oil was fractionated by column chromatography (silica gel, EtOAc-hexanes, 1:9) to obtain 6-methoxy-1-tetralone as ayellowish oil; yield: 0.28 g (91%).