Trifluoroacetic acid → 2,3-Dihydro-6-hydroxy-3-phenylinden-1-one

HRID 331260Notes

Reaction equation

HRID 331260 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:17])/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:3]=[C:4]2[C:5]([CH:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:9][C:8]2=[O:17])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 5356382T5637827

Product 1

HCID 703075012,3-Dihydro-6-hydroxy-3-phenylinden-1-oneYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

(E)-1-(3-Hydroxyphenyl)-3-phenylprop-2-en-1-one (48.7 g, 217 mmol) obtained in Step 1 and CF3COOH (161 mL, 10 eq) were placed into a flask and stirred for 24 h at 80° C. After cooling to room temperature, toluene (200 mL) was added and the solution was concentrated to remove TFA under reduced pressure. The residue was dissolved in EtOAc, washed with H2O, dried over MgSO4, and concentrated in vacuo to obtain the desired product (48.0 g, 99%).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe solution was concentrated
  3. customto remove TFA under reduced pressure
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with H2O
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c6278b364d5449678b2c237d922c7ead
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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