Ammonia → 4-Hydroxyxanthone

HRID 730067Notes

Reaction equation

HRID 730067 reaction equation
C[O:2][C:3]1[C:16]2[O:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[O:17])[C:7]=2[CH:6]=[CH:5][CH:4]=1.B(Br)(Br)Br.N>C(Cl)Cl.CO>[OH:2][C:3]1[C:16]2[O:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[O:17])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 3002414-Methoxyxanthone

Product 1

HCID 6114284-HydroxyxanthoneYield 66.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-methoxy-xanthen-9-one (12 g, 53 mmol) in methylene chloride (100 mL) at 0° C. was added a 1M solution of boron tribromide in methylene chloride (160 mL, 160 mmol) and the mixture was stirred at rt for 2 h. The reaction was slowly poured into a solution of ammonia in methanol (2M). The reaction was concentrated under reduced pressure and the resulting residue was partitioned between 1N HCl and methylene chloride. The organic phase was separated, dried over MgSO4, filtered, and evaporated to afford 7.5 g of Compound 3a, without further purification. MS m/z (M-H)− 243.1.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe resulting residue was partitioned between 1N HCl and methylene chloride
  3. customThe organic phase was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-8d7d01a7fbe64e18bb87cb1ab0620d36
Source dataset
uspto-grants-2009_09
Patent number
US07582650B2

Reaction notes

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