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ChemicalBook CAS DataBase List 6-methoxy-1-tetralone
1078-19-9

6-methoxy-1-tetralone synthesis

11synthesis methods
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%). 1078-19-9.png
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Yield:1078-19-9 95%

Reaction Conditions:

with 1-hydroxy-1H-1,2,3-benziodoxathiole 1,3,3-trioxide;Oxone;cetyltrimethylammonim bromide in water at 20; for 2 h;Green chemistry;chemoselective reaction;

Steps:

IBS-catalysed alcohol oxidation in CTAB micelle; general procedure

General procedure: The alcohol (2 mmol) was added to a solution of IBS (0.02 mmol, 0.01 eq), oxone (2.2 mmol, 1.1 equiv.) and 3 wt% CTAB solution (5 mL). The mixture was stirred at room temperature. The reaction was monitored by TLC. After completion, the solution was extracted with CH2Cl2 (3 × 10 mL). The combined organic phase was then filtered through a pad of silica gel and evaporated under vacuum to afford the desired product.

References:

Liu, Yangyang;Wang, Boliang [Journal of Chemical Research,2014,vol. 38,# 7,p. 427 - 431]

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