Reaktion #75355

Reaktionsgleichung

phenyl magnesium bromide

hydrochloric acid

phenyl magnesium bromide

3-oxocyclohexane-1-acetic acid

→

title compound

Ausbeute 43.2%

3-Hydroxy-3-phenylcyclohexane-1-acetic acid

Ausbeute 43.2%

Lösungsmittel

ether

ether

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat 10° C.
2. 2
   Sonstigeprepared by the method of Bartlett and Woods, J.A.C.S
3. 3
   ExtraktionThe organic extract
4. 4
   Extraktionwas extracted with 150 ml of 1 N sodium hydroxide
5. 5
   ExtraktionThe base extract
6. 6
   Extraktionextracted with 300 ml of ether
7. 7
   ExtraktionThis ether extract
8. 8
   Trocknenwas dried over magnesium sulfate
9. 9
   Sonstigeevaporated to an oil
10. 10
    SonstigeCrystallization from ether

Vorschrift

To a solution of 80 mmol of phenyl magnesium bromide (from 24.2 ml of a 3.3 M solution of phenyl magnesium bromide in ether) in 100 ml of tetrahydrofuran at 10° C. was slowly added 5.0 g (32.1 mmol) of 3-oxocyclohexane-1-acetic acid (prepared by the method of Bartlett and Woods, J.A.C.S. 62, 2933 (1960)) in 25 ml of tetrahydrofuran. The reaction was stirred 1 hr. longer at 25° and then added to 250 ml 1 N hydrochloric acid and 250 ml ether. The organic extract was extracted with 150 ml of 1 N sodium hydroxide. The base extract was reacidified with 200 ml of 1 N hydrochloric acid and extracted with 300 ml of ether. This ether extract was dried over magnesium sulfate and evaporated to an oil. Crystallization from ether gave 3.25 g (43%) of the title compound, MP, 152°, as a pure diastereomer. The mother liquor (4.0 g, 53%) was pure by PMR analysis and contained the other diastereomer. Crystallization of the mother liquor in cyclohexane followed by several recrystallizations gave the other diastereomer of the title compound, MP, 114°-115°.

Quelle