Cyclohexene oxide → rel-(1R,2S)-2-Phenylcyclohexanol

HRID 1085323Notes

Reaction equation

HRID 1085323 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:9]12[O:15][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14]2>O1CCCC1>[C:1]1([C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[OH:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 9246Cyclohexene oxideHCID 178418255HCID 178418255, compound

Product 1

HCID 102793rel-(1R,2S)-2-PhenylcyclohexanolYield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
15 °C

Procedure

A 50-L reactor equipped with a stirrer, a gas bubbler, and an addition funnel was placed under argon, charged with 27.36 L (27.63 mole) of phenylmagnesium bromide (1.0 M), which is known, in tetrahydrofuran and cooled to 15° C. whereupon 235 g (2.37 mole) of CuC1 was added. The resulting mixture was further cooled to -25° C. To this well-stirred mixture was added dropwise over 1.0 hour 1.82 L (18.0 mole, 1766g) of cyclohexene oxide, which is known. After the addition was completed, the mixture was stirred between -10° C. and 0° C. for 4 hours. The reaction mixture was subsequently quenched with 6 L of saturated NH4SO4 solution followed by 4L of water. The organic layer was separated and the aqueous layer was then extracted with 3×6L=18 L of ethyl acetate. The combined organic layers were evaporated in vacuo. When the residue was dissolved into 8 L of methylene chloride, a small aqueous layer separated and was discarded. The organic layer was dried (Na2SO4) and evaporated in vacuo, finally at 0.5 mmHg. The residue on crYstallization from hexane, afforded in 3 crops, 2.96 kg (93%) of (±)-trans-2-phenylcyclohexanol as colorless needles, m.p. 55-57° C.

Workup

  1. customA 50-L reactor equipped with a stirrer
  2. additionwas added
  3. temperatureThe resulting mixture was further cooled to -25° C
  4. additionAfter the addition
  5. customThe reaction mixture was subsequently quenched with 6 L of saturated NH4SO4 solution
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was then extracted with 3×6L=18 L of ethyl acetate
  8. customThe combined organic layers were evaporated in vacuo
  9. dissolutionWhen the residue was dissolved into 8 L of methylene chloride
  10. customa small aqueous layer separated
  11. dry with materialThe organic layer was dried (Na2SO4)
  12. customevaporated in vacuo, finally at 0.5 mmHg
  13. customThe residue on crYstallization from hexane

Sources & evidence

ORD record
ord-1f2f1ee1cfa846e0b60fcd3fba23e14b
Source dataset
uspto-grants-1991_04
Patent number
US05008411

Reaction notes

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