Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.C(Cl)(=O)C(Cl)=O.Cl.[CH3:23][NH:24][O:25][CH3:26]>>[CH3:26][O:25][N:24]([CH3:23])[C:6](=[O:8])[C:5]1[CH:9]=[C:10]([O:14][CH3:15])[C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=1Participants
Procedure
3,4,5-Trimethoxybenzoic acid was allowed to react with oxalyl chloride, and the resulting acid chloride was allowed to react with N,O-dimethylhydroxyamine hydrochloride to obtain N,3,4,5-tetramethoxy-N-methylbenzamide. The resulting compound was allowed to react with 4-phenylbutylmagnesium chloride to obtain 5-phenyl-1-(3,4,5-trimethoxyphenyl)pentan-1-one. The resulting compound was allowed to react with lithium diisopropylamine and methyl2-[4-(bromomethyl)phenoxy]benzoate in the presence of N,N,N′,N″,N″-pentamethyldiethylenetriamine to obtain methyl2-{4-[5-phenyl-2-(3,4,5-trimethoxybenzoyl)pentyl]phenoxy}benzoate. The resulting compound was hydrolyzed with sodium hydroxide to give the title compound having the following physical properties.
Sources & evidence
- ORD record
- ord-ffc278f7405b472a8b837964436c1d1f
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07875745B2
Linked notes
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