[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>CN(C=O)C>[CH2:19]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH2:9][CH2:10][CH2:2][CH2:3][CH3:4])[C:5]([O:7][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:6])[CH2:20][CH2:21][CH2:22][CH3:23]3,4-Dihydroxybenzoic acid (462 mg, 3 mmol) was dissolved in DMF (10 ml). Potassium carbonate (3.73 g, 27 mmol, 9 eq) and 1-bromopentane (1.70 ml, 13.5 mmol, 4.5 eq) were successively added to this solution at room temperature, and the mixture was stirred at 110° C. for 24 hours. This reaction mixture was filtered, and the residual potassium carbonate was washed with ethyl acetate (50 ml). The filtrate was washed with water (15 ml×3) and saturated brine (15 ml). The organic layer was dried over anhydrous sodium sulfate. After the drying agent was filtered off; the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (heaxane/ethyl acetate=95/5) to give pentyl 3,4-dipentyloxybenzoate (912 mg, 83%).
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