Hippuric Acid → HCID 18663606, compound

HRID 1956602Notes

Reaction equation

HRID 1956602 reaction equation
[O:1]([C:8]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:9]=1[CH:10]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([OH:32])(=[O:31])[CH2:21]NC(C1C=CC=CC=1)=O.C([O-])(=O)C.[Na+].S(=O)(=O)(O)O>C(OC(=O)C)(=O)C.O>[F:17][C:16]([F:19])([F:18])[C:14]1[CH:13]=[CH:12][C:9]2[CH:10]=[C:21]([C:20]([OH:32])=[O:31])[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[O:1][C:8]=2[CH:15]=1

Participants

7

Reactant 4

HCID 464Hippuric AcidHCID 1118Sulfuric AcidHCID 517045Sodium AcetateHCID 18663603HCID 18663603, compound

Product 1

HCID 18663606HCID 18663606, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 10.0 g (37.59 mmol) of 2-phenoxy-4-trifluoromethyl-benzaldehyde, 10.09 g (56.40 mmol) of hippuric acid and 3.70 g (45.10 mmol) of sodium acetate in 38 ml of acetic anhydride is heated at 85° C. for 80 minutes, then cooled to 32° C., 19 ml of water are added and the mixture is heated at 65° C. for 30 minutes. After cooling the mixture to approximately 5° C., 19 ml of concentrated sulfuric acid are added dropwise and the mixture is then heated under reflux (bath: 140° C.) for 2 hours. The brown precipitate that forms on cooling is filtered and washed with 50% acetic acid, washed with water until neutral and dried to yield 7.42 g (24.23 mmol)=65% of 3-trifluoromethyl-dibenz[b,f]oxepine-10-carboxylic acid in the form of beige crystals; melting point: 180° C.; 1H-NMR (CDCl3, 200 MHz): 7.2-7.65 (m, 8H); 8.09 (s, 1H).

Workup

  1. temperaturecooled to 32° C.
  2. temperaturethe mixture is heated at 65° C. for 30 minutes
  3. temperatureAfter cooling the mixture to approximately 5° C.
  4. temperaturethe mixture is then heated
  5. temperatureunder reflux (bath: 140° C.) for 2 hours
  6. temperatureon cooling
  7. filtrationis filtered
  8. washwashed with 50% acetic acid
  9. washwashed with water until neutral and
  10. customdried

Sources & evidence

ORD record
ord-b1d40ef8c61b430b8f1dc919f9fdc56c
Source dataset
uspto-grants-1998_07
Patent number
US05780501

Reaction notes

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