[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[C:9]([CH3:18])=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11](OC)=[O:12].O.[OH-].[Na+]>O1CCCC1>[Cl:7][C:8]1[C:9]([CH3:18])=[C:10]([CH2:11][OH:12])[CH:15]=[CH:16][CH:17]=1A solution of lithium aluminium hydride (29.8 mL, 29.8 mmol) in THF was cooled to 0° C., and a solution of methyl 3-chloro-2-methylbenzoate (2.5 g, 13.54 mmol) in Tetrahydrofuran (THF) (20 mL) was added dropwise. The mixture was stirred at 0° C. for half hour, warmed up to RT gradually, and stirred at RT for 2 hours. Water and 6N NaOH (4 ml) were added to quench the reaction. The mixture was filtered and the filtrate was concentrated to afford the crude product as a white solid (2.0 g, 94%). 1H NMR (400 MHz, CDCl3) δppm 7.30˜7.35 (m, 2H), 7.16 (m, 1H), 4.74 (s, 2H), 2.40 (s, 3H).
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