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 one g. of trichloroacetic acid and then the mixture heated at 60° for one 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 three 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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