Benzoic anhydride → HCID 11740970, compound

HRID 1095283Notes

Reaction equation

HRID 1095283 reaction equation
[C:1]([O:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=[O:25])C1C=CC=CC=1.[Na+].[CH3:28][O:29][C:30]1[CH:31]=C(O)C=[C:34]([O:38][CH3:39])[C:35]=1[O:36][CH3:37].[CH2:41]([C:48]#N)[C:42]1C=CC=CC=1>C(OCC)(=O)C.[Cl-].[Zn+2].[Cl-]>[C:11]1([C:10]2[O:9][C:1]3[C:2]([C:7](=[O:25])[C:6]=2[C:5]2[CH:4]=[CH:3][CH:48]=[CH:41][CH:42]=2)=[C:34]([O:38][CH3:39])[C:35]([O:36][CH3:37])=[C:30]([O:29][CH3:28])[CH:31]=3)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 7167Benzoic anhydrideHCID 8794PhenylacetonitrileHCID 695053,4,5-TrimethoxyphenolHCID 517055Sodium Benzoate

Product 1

HCID 11740970HCID 11740970, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
97.5 °C

Procedure

The title compound is prepared from heating a mixture of ω-phenyl-6-hydroxy-2,3,4-trimethoxy-acetophenone (0.996 g, 3.3 mmol), benzoic anhydride (6 g, 13.3 mmol) and sodium benzoate (6.5 g, 22.5 mmol) at 180-190° C. for 6 hr according to the published procedure (Wu, E S C et al. J. Med. Chem. 1988, 32, 183-192). Similar to the preparation ω-phenylresacetophenone (Wu, E S C et al. J. Med. Chem. 1987, 30, 788-792), ω-phenyl-6-hydroxy-2,3,4-trimethoxy-acetophenone is, in turn, obtained from adding anhydrous zinc chloride to a solution of 3,4,5-trimethoxyphenol and benzyl cyanide in ethyl acetate followed by bubbling HCl into the reaction mixture at room temperature and then heating at 95-100° C. with water.

Workup

  1. temperaturefrom heating
  2. customobtained
  3. customby bubbling HCl into the reaction mixture at room temperature

Sources & evidence

ORD record
ord-8a5fcb56bec4460e8dd8ad2593dafc2c
Source dataset
uspto-grants-2012_03
Patent number
US08138165B2

Reaction notes

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