Benzoic acid, 4,4'-carbonylbis-, dimethyl ester → HCID 16086976, compound

HRID 1724113Notes

Reaction equation

HRID 1724113 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=2)=O)=[CH:7][CH:6]=1)=[O:4].Cl.[NH2:24][OH:25].C([O-])(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=2)=[N:24][OH:25])=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 299003Benzoic acid, 4,4'-carbonylbis-, dimethyl esterHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 517045Sodium Acetate

Product 1

HCID 16086976HCID 16086976, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6 (2.33 g, 7.81 mmol), HCl-H2NOH (1.63 g, 23.4 mmol) and sodium acetate (1.92 g, 23.4 mmol) in Ethanol (80 ml) was heated for 24 h under reflux. The mixture was allowed to cool to RT, and half concentrated NaHCO3-solution (200 ml) was added. The aqueous phase was extracted with Et2O, the unified organic phases were washed with saturated solutions of NaHCO3 and NaCl, and dried over Na2SO4. The solvent was removed, and the crude product is crystallized from ethanol. 2.15 g (88%) of compound 7 are obtained as a colorless solid. Melting point 177-178° C.; IR (KBr) 3190, 2920, 1700, 1585 cm−1; 1H-NMR (CDCl3) δ 8.50 (sbr, 1H), 8.16 (d, 8.6 Hz, 2H), 8.00 (d, 8.6 Hz, 2H), 7.51 (d, 8.6 Hz, 2H), 7.47 (d, 8.6 Hz, 2H), 3.96 (s, 3H), 3.93 (s, 3H); MS (EI) m/z 313 (M+). Anal. calc. for C17H15NO5: C, 65.17; H, 4.83; N, 4.47. Found C, 65.14; H, 4.78; N, 4.47.

Workup

  1. temperaturewas heated for 24 h
  2. temperatureunder reflux
  3. extractionThe aqueous phase was extracted with Et2O
  4. washthe unified organic phases were washed with saturated solutions of NaHCO3 and NaCl
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed
  7. customthe crude product is crystallized from ethanol

Sources & evidence

ORD record
ord-d04d850c536649059edd48c211af3d6c
Source dataset
uspto-grants-2009_02
Patent number
US07485742B2

Reaction notes

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