Water → 4-Methoxyxanthone

HRID 730066Notes

Reaction equation

HRID 730066 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[O:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.B(F)(F)F.CCOCC.O>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]2[O:5][C:6]3[C:7](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:8](=[O:10])[C:15]=2[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8000Boron trifluoride etherateHCID 9845Trifluoroacetic anhydrideHCID 5786892-(2-Methoxyphenoxy)benzoic acid

Product 1

HCID 3002414-MethoxyxanthoneYield 79.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 2-(2-methoxy-phenoxy)-benzoic acid (16.8 g, 68.8 mmol) in methylene chloride (100 mL) at 0° C. was added dropwise trifluoroacetic anhydride (12.7 mL, 89.4 mmol), and the reaction was stirred for 30 min at 0° C. At that time, boron trifluoride diethyl etherate (1.29 mL, 10.3 mmol) was added dropwise. The reaction was stirred overnight at rt, poured into H2O, and washed with brine. The organic phase was dried over MgSO4, filtered, and concentrated to give 12.4 g (54.8 mmol) of Compound 2a.

Workup

  1. stirringThe reaction was stirred overnight at rt
  2. washwashed with brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-24cbce89319a47ac8d523e3c9b2eee61
Source dataset
uspto-grants-2009_09
Patent number
US07582650B2

Reaction notes

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