반응 #468719

반응 방정식

sodium borohydride

4,4-dimethyl-1-tetralone

water

→

1,2,3,4-tetrahydro-4,4-dimethyl-1-naphthol

용매

methanol

methanol toluene

반응 조건

후처리

1. 1
   기타the organic layer was separated
2. 2
   건조dried over magnesium sulfate
3. 3
   여과filtered
4. 4
   기타evaporated under reduced pressure
5. 5
   기타to leave a light yellow oil
6. 6
   기타This was purified by silica gel column chromatrography
7. 7
   세척eluting with ethyl acetate:hexane (1:9)

실험 절차

To a stirred suspension of sodium borohydride (3.5 g, 93 mmoles) in dry methanol (50 ml) at 0° C. under a nitrogen atmosphere was added a solution of 4,4-dimethyl-1-tetralone (10 g, 57.4 mmoles) in dry methanol:toluene (1:3) dropwise over a 45 minute period. After this time the mixture was allowed to warm to room temperature, and then two volumes of water were added. After stirring for 1 hour, the organic layer was separated, dried over magnesium sulfate, filtered, and evaporated under reduced pressure to leave a light yellow oil. This was purified by silica gel column chromatrography eluting with ethyl acetate:hexane (1:9) to give 1,2,3,4-tetrahydro-4,4-dimethyl-1-naphthol as a colorless oil. (9.89 g, 98%).

출처