Trifluoroacetic acid → HCID 12505004, compound

HRID 1665850Notes

Reaction equation

HRID 1665850 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([O:18][Si](C)(C)C)[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])=[CH:5][CH:4]=1.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>O>[OH:18][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:10]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:11]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 57826337HCID 57826337, compound

Product 1

HCID 12505004HCID 12505004, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

30 g (0.091 mol) of 2-(4-methoxyphenyl)-1-phenyl-2-trimethylsilanyloxy-ethanone prepared in Step 2 was added to 50 mL of an aqueous 90% trifluoroacetic acid solution and the resulting reaction solution was stirred at room temperature for 2 hours. An ice bath was placed and the resulting reaction solution was neutralized with addition of sodium carbonate. Then, 200 mL of ethyl acetate and 100 mL of water were added to dilute the solution, followed by separation of layers. The obtained organic layer was washed twice with 100 mL of a saturated sodium bicarbonate solution and then successively washed twice with 100 mL of a brine solution. The organic layer thus obtained was dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 17.25 g of a final product which was then recrystallized from ethyl acetate and hexane, to give 14.38 g (yield: 65%) of pure 2-hydroxy-2-(4-methoxyphenyl)-1-phenyl-ethanone.

Workup

  1. customthe resulting reaction solution
  2. customAn ice bath was placed
  3. customthe resulting reaction solution
  4. additionto dilute the solution
  5. customfollowed by separation of layers
  6. washThe obtained organic layer was washed twice with 100 mL of a saturated sodium bicarbonate solution
  7. washsuccessively washed twice with 100 mL of a brine solution
  8. customThe organic layer thus obtained
  9. dry with materialwas dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee074e53166f4133a18747b1dabd61d7
Source dataset
uspto-grants-2011_10
Patent number
US08039634B2

Reaction notes

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