4,4-dimethyl-6-methoxy-1-tetralone synthesis
- Product Name:4,4-dimethyl-6-methoxy-1-tetralone
- CAS Number:23203-51-2
- Molecular formula:C13H16O2
- Molecular Weight:204.26
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
1073-13-8
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23203-51-2
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4255-62-3
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23203-51-2
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77630-12-7
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23203-51-2
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64230-02-0
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23203-51-2
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