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ChemicalBook CAS DataBase List 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydronaphthalene
6683-46-1

1,1,4,4-Tetramethyl-1,2,3,4-tetrahydronaphthalene synthesis

8synthesis methods
2,5-dichloro-2,5- dimethylhexane (300 mg, 1.64 mmol, 1 eq) was dissolved in dry benzene (25 mL). Then added AlCl3 (22.0 mg, 0.164 mmol, 0.1 eq) to the solution, which was stirred at reflux for 16 hours. The reaction was stopped with 3M HCl (5 mL) and extracted with hexanes (10 mL x 3). The combined organic layer was washed with brine, dried with Na2S04, filtered, and concentrated in vacuo. Finally, the crude was purified by flash chromatography (100% hexanes) to obtained the colourless oil (1,1,4,4-Tetramethyl-1,2,3,4-tetrahydronaphthalene).Yield=91%
1,2,3,4-TETRAHYDRO-1,1,4,4-TETRAMETHYLNAPHTHALENE
-

Yield: 91%

Reaction Conditions:

with aluminum (III) chloride for 16 h;Reflux;

Steps:

2 l,l,4,4-tetramethyl-l,2,3,4-tetrahydronaphth.alene (18):
l,l,4,4-tetramethyl-l,2,3,4-tetrahydronaphth.alene (18): 2,5-dichloro-2,5- dimethylhexane (300 mg, 1.64 mmol, 1 eq) was dissolved in dry benzene (25 mL). A1C13 (22.0 mg, 0.164 mmol, 0.1 eq) was added to the solution, which was stirred at reflux for 16 hours. The reaction was quenched with 3M HC1 (5 mL) and extracted with hexanes (10 mL x 3). The combined organic layer was washed with brine, dried with Na2S04, filtered, and concentrated in vacuo. The crude was purified by flash chromatography (100% hexanes) to give 18 (309 mg, 91% yield) as a colourless oil. Characterization data for 18: <5H (500MHz, CDC13) 1.33 (s, 12H), 1.74 (s, 4H), 7.16-7.19 (m, 2H), 7.34-7.36 (m, 2H, J 2 Hz and 8.4 Hz).<5c (500MHz, CDC13) 31.9, 34.2, 35.1, 125.5, 126.5, 144.8.

References:

HARO PHARMACEUTICAL INC.;THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING/MCGILL UNIVERSITY;UNIVERSITE DE MONTREAL;BETTOUN, David;MARTINEZ, Eduardo, J.;GLEASON, James;MADER, Sylvie;XING, Shuo WO2015/188015, 2015, A1 Location in patent:Page/Page column 31

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