Hydrochloric Acid → HCID 12223605, compound

HRID 374017Notes

Reaction equation

HRID 374017 reaction equation
C([OH:3])C.[OH-].[Na+].[CH3:6][C:7]1[C:8]2[O:27][C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[C:9]=2[C:10]2[C:11](=[O:24])N(C3C=CC(C)=CC=3)[C:13](=[O:16])[C:14]=2[CH:15]=1.Cl>O.C(OCC)(=O)C>[CH3:6][C:7]1[CH:15]=[C:14]2[C:13](=[O:3])[O:16][C:11](=[O:24])[C:10]2=[C:9]2[C:25]3[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=3[O:27][C:8]=12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 19808854HCID 19808854, compound

Product 1

HCID 12223605HCID 12223605, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

5 ml of ethanol and 1.2 ml of a 5 N aqueous sodium hydroxide solution were added to 200 mg of 5-methyl-2-(4-methylphenyl)-1H-benzofuro[3,2-e]isoindole-1,3(2H)-dione. The mixture was refluxed for 30 minutes. Thereto was added 1.2 ml of concentrated hydrochloric acid. The resulting mixture was refluxed for 1 hour and then cooled to room temperature. Then, thereto were added 20 ml of ethyl acetate and 10 ml of water. The organic layer was separated, washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was mixed with 2.0 ml of acetic anhydride. The mixture was refluxed for 30 minutes, and then concentrated to dryness under reduced pressure. The residue was washed with diethyl ether and dried to obtain 140 mg (yield: 91%) of 4-methyldibenzofuran-1,2-dicarboxylic anhydride as light yellow crystals.

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. temperatureThe resulting mixture was refluxed for 1 hour
  3. customThe organic layer was separated
  4. washwashed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. additionThe residue was mixed with 2.0 ml of acetic anhydride
  8. temperatureThe mixture was refluxed for 30 minutes
  9. concentrationconcentrated to dryness under reduced pressure
  10. washThe residue was washed with diethyl ether
  11. customdried

Sources & evidence

ORD record
ord-0bb1181849524c28b5fc5e722a5cf0d3
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

Loading…