1,3-Benzenediol,5-methyl-4-[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl]- synthesis

Yield: 24%

Reaction Conditions:

with boron trifluoride diethyl etherate in 1,4-dioxane at 0 - 20; for 3 h;

Steps:

4.2.1. General procedure A: Alkylation
General procedure: BF₃·Et₂O was slowly added dropwise, to a stirred solution of polyhydroxy or polymethoxy phenols and alkyl alchol in dioxane at 0°C. After the addition was completed, the stirring was continued for 3h at room temperature. The mixture was poured water and extracted with EtOAc. The organic layer was dried over Na₂SO₄ and filtered. The solvent was evaporated under reduced pressure. The crude was chromatographed on silica gel.

References:

Kamauchi, Hitoshi;Oda, Takumi;Horiuchi, Kanayo;Takao, Koichi;Sugita, Yoshiaki [Bioorganic and Medicinal Chemistry,2020,vol. 28,# 1,art. no. 115156]