C[O:2][CH:3](OC)[CH:4]([CH3:13])[CH2:5][CH2:6][CH:7]([O:11][CH3:12])[CH:8]([CH3:10])[CH3:9].ClC(Cl)(Cl)C(O)=O.[OH-].[Na+].[BH4-].[Na+]>CO.O.O1CCCC1>[OH:2][CH2:3][CH:4]([CH3:13])[CH2:5][CH2:6][CH:7]([O:11][CH3:12])[CH:8]([CH3:9])[CH3:10]A solution of 10.9 g. of 1,1,5-trimethoxy-2,6-dimethylheptane in 200 ml. of tetrahydrofuran and 60 ml. of water is treated with 1 g. of trichloroacetic acid and then the mixture heated at 60° for 1 hour. After cooling, there is added 40 ml. of 2N sodium hydroxide in methanol followed by 2 g. of powdered sodium borohydride. The reaction mixture is stirred at room temperature for 3 hours and then concentrated and extracted with ether. The ethereal extracts are evaporated under reduced pressure to give crude 1-hydroxy-5-methoxy-2,6-dimethylheptane which can be purified by distillation.
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