Reaktion #742286

Reaktionsgleichung

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

sodium borohydride

→

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

Ausbeute 94.1%

Lösungsmittel

isopropanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturrefluxed for 30 minutes
2. 2
   Sonstigequenched with acetone ((CH3)2CO)
3. 3
   SonstigeThe organic layer was separated
4. 4
   Einengenconcentrated

Vorschrift

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

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