4,4-dimethyl-6-methoxy-1-tetralone synthesis

10synthesis methods

Product Name:4,4-dimethyl-6-methoxy-1-tetralone
CAS Number:23203-51-2
Molecular formula:C13H16O2
Molecular Weight:204.26

1,1-dimethyl-7-methoxy-1,2,3,4-tetrahydronaphthalene

23203-50-1
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23203-51-2
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Yield:23203-51-2 93%

Reaction Conditions:

in water;acetic acid;

Steps:

General Procedure B: 6-Methoxy-4,4-dimethyl-1,2,3,4-tetrahydronaphthalene-1-one (Intermediate 9)

General Procedure B: 6-Methoxy-4,4-dimethyl-1,2,3,4-tetrahydronaphthalene-1-one (Intermediate 9) A solution of 7-methoxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene (Intermediate 8, 1.65 g, 8.7 mmol) in 7.5 mL of glacial acetic acid was cooled to 0° C. and treated with a solution of chromium trioxide (2 g, 20 mmol) in 8 mL of acetic acid and 7 mL of water. The reaction mixture was then allowed to warm to ambient temperature and stirred overnight. It was diluted with water and extracted with diethyl ether (*2). The combined organic phase was washed with water (*1), saturated aqueous sodium bicarbonate (*1) and brine (*1), dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title compound (1.64 g, 93%) as a yellow oil. ¹H-NMR (300 MHz, CDCl₃): δ1.34(s, 6H), 1.96(t, J=7.1 Hz, 2H), 2.64(t, J=7.1 Hz, 2H), 3.83(s, 3H), 6.77(dd, J=2.6, 8.7 Hz, 1H), 6.83(d, J=2.5 Hz, 1H), 7.98(d, J=8.7 Hz, 1H).

References:

US6313107,2001,B1