Acetone → HCID 57554489, compound

HRID 551917Notes

Reaction equation

HRID 551917 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([OH:13])=[O:12].[CH3:14][C:15]([CH3:17])=O>C(O)(C(F)(F)F)=O.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>[CH3:14][C:15]1([CH3:17])[O:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=2[C:11](=[O:13])[O:12]1

Participants

5

Reactant 2

HCID 180AcetoneHCID 124904-Hydroxyisophthalic acid

Product 1

HCID 57554489HCID 57554489, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 9845Trifluoroacetic anhydrideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 4-hydroxyisophtalic acid (Aldrich, 5.0 g, 27.5 mmol) in acetone (10 mL), TFA (30 mL) and TFAA (10 mL) was heated at 100° C. for 24 hrs. The reaction mixture was concentrated under reduced pressure. The residue was taken up with an aqueous solution of HCl (100 mL, 1N) and extracted with EtOAc (3×200 L); The combined organic layers were dried over MgSO4 and the solvents were removed under reduced: pressure. The crude compound was recrystallized in Et2O (50 mL) to give 4.67 g (77%) of the title compound as a beige powder. 1H NMR (DMSO-d6) δ: 8.37 (d J=1.9 Hz, 1H), 8.19 (dd, J=2.2 and 8.7 Hz, 1H), 7.23 (d, J=8.3 Hz, 1H), 1.72 (s, 6H). HPLC, Rt: 2.40 min (purity: 95.7%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with EtOAc (3×200 L)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customthe solvents were removed
  5. customThe crude compound was recrystallized in Et2O (50 mL)

Sources & evidence

ORD record
ord-5239bc217de14bc19f5e1c209b28bbc8
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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