ChemicalBook CAS DataBase List Honokiol

Honokiol synthesis

9synthesis methods

Product Name:Honokiol
CAS Number:35354-74-6
Molecular formula:C18H18O2
Molecular Weight:266.33

1-methoxy-4-(2-methoxy-5-prop-2-enyl-phenyl)-2-prop-2-enyl-benzene

68592-18-7
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35354-74-6
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Yield:35354-74-6 97%

Reaction Conditions:

with aluminum (III) chloride at -5 - 0; for 0.333333 h;

Steps:

Synthesis of 3',5-diallylbiphenyl-2,4'-diol (1)

The solution of 30,5-diallyl-2,40-dimethoxy biphenyl 3 (0.5 g, 1.69 mmol) in DMS (2 ml) was added slowly to asolution of AlCl3 (678 mg, 5 mmol) in DMS (15 ml) at 5 C and the temperature was maintained between 5 and 0 C for 20 min. The reactionwas then poured in ice cold water and extracted with EtOAc (20 ml 3),washed with H2O (10 ml), dried over anhydrous Na2SO4, and concentrated invacuo. Crystallization of the residue in ethyl acetate/hexane (3:7) afforded 1 inquantitative yield 97% (0.44 g). 1H NMR (200 MHz, CDCl3): d 3.37 (d, J = 6.4 Hz,2H), 3.48 (d, J = 6.3 Hz, 2H), 5.03-5.24 (m, 4H), 5.98-6.06 (m, 2H), 6.90-6.94(m, 2H), 7.08 (d, J = 8.4 Hz, 2H), 7.3 (d, J = 7.1 Hz, 2H); 13C NMR (125 MHz,CDCl3): 151.09, 137.58, 133.24, 131.39, 131.16, 130.28, 129.87, 128.84, 128.54,116.75, 115.84, 115.64, 39.37, 35.08; ESI-MS: 266 (M+).

References:

Srinivas, Jada;Singh, Parvinder Pal;Varma, Yogesh Kumar;Hyder, Irfan;Kumar, Halmuthur M. Sampath [Tetrahedron Letters,2014,vol. 55,# 31,p. 4295 - 4297]