Water → (S)-3-Phenylcyclohexanone

HRID 1814730Notes

Reaction equation

HRID 1814730 reaction equation
O1CCOCC1.O.[C:8]1(=[O:14])[CH2:13][CH2:12][CH2:11][CH:10]=[CH:9]1.[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(OCC)(=O)C>[C:15]1([C@H:10]2[CH2:11][CH2:12][CH2:13][C:8](=[O:14])[CH2:9]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 135942-Cyclohexen-1-oneHCID 312751,4-DioxaneHCID 66827Phenylboronic Acid

Product 1

HCID 11116555(S)-3-Phenylcyclohexanone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

1 ml of dioxane, 0.1 ml of distilled water and 0.4 mmol of cyclohexenone are added to 3.1 mg of Rh(acac)(C2H4)2, 0.012 mmol of compound I.1 and 2 mmol of phenylboronic acid under argon. The reaction mixture is heated at 100° C. for 5 hours. After it has returned to room temperature, the solvents are evaporated off under reduced pressure. The residue obtained is dissolved in 20 ml of ethyl acetate, washed with 5 ml of saturated aqueous sodium hydrogencarbonate solution and then dried over sodium sulfate. The solvents are then evaporated off under reduced pressure. The product is purified by filtration on silica to isolate (S)-3-phenylcyclohexanone, which is characterized by the 1H NMR spectrum below.

Workup

  1. customhas returned to room temperature
  2. customthe solvents are evaporated off under reduced pressure
  3. customThe residue obtained
  4. washwashed with 5 ml of saturated aqueous sodium hydrogencarbonate solution
  5. dry with materialdried over sodium sulfate
  6. customThe solvents are then evaporated off under reduced pressure
  7. filtrationThe product is purified by filtration on silica

Sources & evidence

ORD record
ord-d475f4a6894c44728eacce6d2bcc0b7a
Source dataset
uspto-grants-2005_04
Patent number
US06878665B2

Reaction notes

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