[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)[C:3]=1[C:4](OC)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1.CCOCC>[OH:5][CH2:4][C:3]1[C:2]([CH3:1])=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:12][O:13][C:14]1[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=1To a cooled (0° C.) solution of methyl 2-methyl-6-[(3-hydroxy-phenoxy)-methyl]-benzoate (220 mg, 0.76 mmol, example 5) in THF (2 mL) is added lithium aluminum hydride solution (1.5 mL, 1 M in THF). The resulting solution is stirred for 10 min then warmed to room temperature and stirred for 40 min. This solution is then cooled to 0° C. and water (75 mL) added, dropwise, followed by sodium hydroxide solution (75 mL, SN) and water (75 mL). The resulting suspension is diluted with ether, filtered through celite and the solid washed thoroughly with methanol (until the solid is free of product by TLC analysis). The combined filtrates are concentrated under vacuum to give the title compound as a white solid. MS (EI) 244 (M)+.
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