Reaction #742286

Reaction equation

1,4-Dimethyl-bicyclo[3.2.1]octan-3-one

sodium borohydride

→

1,4-dimethyl-bicyclo[3.2.1]octan-3-ol

Yield 94.1%

Solvents

isopropanol

Conditions

Workup

1. 1
   Temperaturerefluxed for 30 minutes
2. 2
   Otherquenched with acetone ((CH3)2CO)
3. 3
   OtherThe organic layer was separated
4. 4
   Concentrationconcentrated

Procedure

1,4-Dimethyl-bicyclo[3.2.1]octan-3-one (260 g, 1.7 mol, obtained as above in EXAMPLE III) was added to a suspension of sodium borohydride (NaBH4, 19 g, 0.5 mol) in isopropanol ((CH3)2CHOH, 400 mL), and refluxed for 30 minutes. The reaction mixture was cooled to room temperature, and quenched with acetone ((CH3)2CO) followed by acetic acid. The organic layer was separated and concentrated to provide crude 1,4-dimethyl-bicyclo[3.2.1]octan-3-ol (250 g, 1.6 mol), which was then added to a solution of acetic anhydride ((CH3CO)2O, 192 g, 1.9 mol) and Na2CO3 (4 g, 0.036 mol) and aged at 60° C. for 6 hours. The reaction mixture was subsequently washed with water followed by a Na2CO3 solution. Fractional distillation of the organic layer provided acetic acid 1,4-dimethyl-bicyclo[3.2.1]oct-3-yl ester (159 g) having a boiling point of 88° C. at a pressure of 15 mmHg

Source