Ethyl bromoacetate → Ethyl(9-Oxoxanthen-2-oxy)acetate

HRID 1197191Notes

Reaction equation

HRID 1197191 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1.Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+].C1C=CC=CC=1.CCO>CC(C)=O.CN(C=O)C>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][O:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1)[CH3:23]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 747082-HydroxyxanthoneHCID 21965192Npc112006

Product 1

HCID 15222242Ethyl(9-Oxoxanthen-2-oxy)acetate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-hydroxyxanthone (4.39 g, 20.6 mmol) prepared as described above, ethyl bromoacetate (4.5 mL, 40 mmol), and anhydrous potassium carbonate (16.6 g, 0.12 mol) in acetone (200 mL) plus DMF (10 mL) was refluxed for 6 hours. The cooled reaction mixture was filtered to remove inorganic salts, washed with acetone (2×50 mL), concentrated, and placed under hexane whereupon crystals formed. Yield: 4.87 g (79%), TLC: Rf 0.81 [one spot, benzene-EtOH (20:3)], m.p. 122°-123° C.; 1H-NMR (CDCl3, 200 MHz) 8.32 (d,J=7.9 Hz, 1H), 7.63-7.75 (m, 2H), 7.33-7.50 (m, 4H), 4.74 [s, 2H, OCH2 (C=O)], 4.29 (q,J=7.1 Hz, 2H), 1.32 (t,J=7.1 Hz, 3H).

Workup

  1. customprepared
  2. temperaturewas refluxed for 6 hours
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. customto remove inorganic salts
  6. washwashed with acetone (2×50 mL)
  7. concentrationconcentrated
  8. customformed

Sources & evidence

ORD record
ord-89002be04c364f378b23f5c051d84a23
Source dataset
uspto-grants-1992_05
Patent number
US05117009

Reaction notes

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