Reaction #75355

Reaction equation

phenyl magnesium bromide

hydrochloric acid

phenyl magnesium bromide

3-oxocyclohexane-1-acetic acid

→

title compound

Yield 43.2%

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

Yield 43.2%

Solvents

ether

ether

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   Otherat 10° C.
2. 2
   Otherprepared by the method of Bartlett and Woods, J.A.C.S
3. 3
   ExtractionThe organic extract
4. 4
   Extractionwas extracted with 150 ml of 1 N sodium hydroxide
5. 5
   ExtractionThe base extract
6. 6
   Extractionextracted with 300 ml of ether
7. 7
   ExtractionThis ether extract
8. 8
   Dryingwas dried over magnesium sulfate
9. 9
   Otherevaporated to an oil
10. 10
    OtherCrystallization from ether

Procedure

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°.

Source