[OH:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[C:4]([CH3:12])[C:3]=1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](OC)=[O:23].[BH4-].[Na+].[Cl-].[Al+3].[Cl-].[Cl-].Cl>O1CCCC1.O>[OH:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[C:4]([CH3:12])[C:3]=1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23]In tetrahydrofuran (1.8 l) was dissolved methyl 10-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)decanoate (881 g, 2.5 mol.). To the solution was added a suspension of sodium borohydride (340 g, 9 mol.) in tetrahydrofuran (10.7 l), and the mixture was stirred. To the resulting suspension was added water (75 ml, 4.16 mol.). Aluminum chloride (400 g, 3 mol.) was dissolved in tetrahydrofuran (6.0 l). The solution was added dropwise to the above-mentioned suspension at a given rate in the course of 90 minutes, during which period the inner temperature of the reaction mixture was kept at 25±2° C. Then, the reaction mixture was stirred at the same temperature for further 30 minutes, which was then cooled to about 15° C. To the reaction mixture was added water (22 l) dropwise to cause decomposition, to which was then added dropwise hydrochloric acid (2.7 l). The mixture was subjected to extraction twice with 9 l each portion of toluene. Then, the toluene layers were combined and washed with a 5% aqueous solution of sodium hydrogen carbonate (4.4 l), followed by further washing with water (4.4 ). The toluene layer was concentrated under reduced pressure to obtain 10-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)decan-1-ol (805 g, 2.48 mol., yield 99.2%) as an oily product.
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