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1
Synthesize Find similar 92%
With boron tribromide in dichloromethane
T=-15 - 20°C; 1.5 h; Inert atmosphere; Hide Experimental Procedure
Synthesize Find similar
Rx-ID: 271814 Find similar reactions
Sisa, Miroslav; Dvorakova, Marcela; Vanek, Tomas
Tetrahedron, 2017 , vol. 73, # 35 p. 5297 - 5301 Title/Abstract Full Text View citing articles Show Details
1,3-Dihydroxy-5-alkylbenzenes (3, 4, 5): general method
General procedure: To the solution of 1,3-dimethoxy-5-alkylbenzenes 8, 11, and 12,respectively, in dry dichloromethane was added dropwise 2.2 eq. of BBr3 (1 M solution in dichloromethane) at 15 °C and the reaction was stirred under argon atmosphere with temperature rising to r.t. over 1.5 h. The mixture was quenched with water, neutralized with NaHCO3 and extracted with dichloromethane. The organic phase was washed with water and brine and dried over MgSO4. After concentration in vacuo, the crude product was purified by silica gel column chromatography with petrol ether:ethyl acetate (9:1) as an eluent. The yields were 92percent for olivetol (3), 82percent for grevillol (4), and 86percent for cardol (adipostatin A, 6), respectively. 81%
With hydrogen bromide; acetic acid
3 h; Heating;
Alonso, Emma; Ramon, Diego J.; Yus, Miguel
Journal of Organic Chemistry, 1997 , vol. 62, # 2 p. 417 - 421 Title/Abstract Full Text View citing articles Show Details
61%
With lithium; ethylenediamine in tetrahydrofuran
T=8°C; 14 h;
Shindo, Takeyuki; Fukuyama, Yasuaki; Sugai, Takeshi
Synthesis, 2004 , # 5 p. 692 - 700 Title/Abstract Full Text View citing articles Show Details