Process for synthesizing of hydroquinone derivatives with heptadecatrienyl side chain

A method of preparing a hydroquinone derivative with heptadecatrienyl side chain, comprising:

• (a) activating 1,4-dimethoxybenzene with n-butyl lithium in tetrahydrofuran, and then reacting with 1,10-dibromodecane at room temperature to obtain a compound of formula (1)
• (b) reacting the compound of formula (1) with boron tribromide to obtain a compound of formula (2)
• (c) reacting the compound of formula (2) with acetic anhydride in pyridine to obtain a compound of formula (3)
• (d) reacting the compound of formula (3) with sodium iodide to obtain a compound of formula (4)
• (e) treating the compound of formula (4) with sodium bicarbonate in dimethyl sulfoxide and benzene, and extracting with 0.1N HCl and saturated sodium chloride to obtain a compound of formula (5)
• (f) subjecting the compound of formula (5) and heptadien-1-triphenylphosphonium iodide to a Wittig reaction and then a deacetylation reaction to obtain a hydroquinone derivative with heptadecatrienyl side chain, which is a compound of formula (11)
• (g) reacting the compound of formula (11) with sodium methoxide in methanol at room temperature to obtain a compound of formula (12)
• wherein the compound of formula (11) is reacted with the sodium methoxide in methanol at least 20 hours, then extracted with benzene, and organic layers are combined and evaporated to dryness under reduced pressure, then purified by a silica gel column to obtain the compound of formula (12).