Acetone → HCID 59839591, compound

HRID 551975Notes

Reaction equation

HRID 551975 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.[CH3:25][C:26]([CH3:28])=O>C(O)(C(F)(F)F)=O>[CH3:25][C:26]1([CH3:28])[O:11][C:4]2[CH:3]=[C:2]([CH3:1])[CH:10]=[CH:9][C:5]=2[C:6](=[O:8])[O:7]1

Participants

5

Reactant 3

HCID 180Acetone2×HCID 57882-Hydroxy-p-toluic acidHCID 9845Trifluoroacetic anhydride

Product 1

HCID 59839591HCID 59839591, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred suspension of 4-methylsalicylic acid (50 g, Aldrich) in TFA (320 mL) under nitrogen was added TFAA (105 mL) followed by dry acetone (60 mL). The reaction mixture was heated to 65° C. for 5 hours. At this time was added another portion of acetone (50 mL) and heating was continued for 15 hours. The solvent was removed under reduced pressure and the residue was taken up with Et2O (250 mL). The organic layer was washed with a 10% aqueous solution of NaHCO3 (2×100 mL), brine and dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by chromatography (Pet Ether/EtOAc 98/2) to give 17 g (27%) of the titled compound as a liquid. TLC-Pet. Ether/EtOAc (9/1): Rf=0.8.

Workup

  1. temperatureheating
  2. customThe solvent was removed under reduced pressure
  3. washThe organic layer was washed with a 10% aqueous solution of NaHCO3 (2×100 mL), brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by chromatography (Pet Ether/EtOAc 98/2)

Sources & evidence

ORD record
ord-b357804174184f38962aece029ff41b3
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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