Potassium Carbonate → 1,2-Propanediol, 1-phenyl-

HRID 1244196Notes

Reaction equation

HRID 1244196 reaction equation
C/C=C/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:10](=[O:13])([O-])[O-].[K+].[K+].O.[CH3:17][C:18](C)=[O:19]>[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[C:4]1([CH:10]([OH:13])[CH:18]([OH:19])[CH3:17])[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 252325trans-beta-METHYLSTYRENEHCID 18366337Propan-2-one--water (1/1)

Product 1

HCID 158251,2-Propanediol, 1-phenyl-Yield 85%

Reagents, catalysts & solvents 1

HCID 178511488HCID 178511488, compoundCatalyst

Procedure

To 3.5 ml of a water-acetone (1:1) solvent were added 66.6 mg of the osmium oxide carried by the carrier of the present invention obtained in Example 4, 21.5 mg of 1,4-bis(9-o-dihydroquinidil)phthalazine, 362.2 mg of potassium ferricyanide and 152.0 mg of potassium carbonate, followed by reacting at 30° C. for 1 hour while stirring. And 59.0 mg of trans-β-methylstyrene dissolved in 1.5 ml of a water-acetone (1:1) solvent were added to the reaction solution and followed by reacting for another 2 hours while stirring. And further, 362.2 mg of potassium ferricyanide and 152.0 mg of potassium carbonate were added to the reaction solution and followed by reacting for another 2 hours while stirring. After the reaction was terminated by adding methanol, the filtrate obtained by filtrating the reaction solution was concentrated to some extent. The obtained product was dissolved in 5 ml of methylene chloride and filtrated using Celite. The filtrate was concentrated and purified using a silica gel thin-layer chromatography, to obtain 70.6 mg of a desired diol, 1-phenyl-1,2-propane diol (yield 85%) (97% ee).

Workup

  1. additionwere added to the reaction solution
  2. waitby reacting for another 2 hours
  3. stirringwhile stirring
  4. waitby reacting for another 2 hours
  5. stirringwhile stirring
  6. customAfter the reaction was terminated
  7. additionby adding methanol
  8. customthe filtrate obtained
  9. filtrationby filtrating the reaction solution
  10. concentrationwas concentrated to some extent
  11. dissolutionThe obtained product was dissolved in 5 ml of methylene chloride
  12. filtrationfiltrated
  13. concentrationThe filtrate was concentrated
  14. custompurified

Sources & evidence

ORD record
ord-e2efda77ee47422d90340c2a508c8909
Source dataset
uspto-grants-2006_10
Patent number
US07122499B2

Reaction notes

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