Potassium Carbonate → Dimethyl 4-[4-(2-benzoxazolyl)benzyloxy]-benzylidenemalonate

HRID 616525Notes

Reaction equation

HRID 616525 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=1.[OH:18][C:19]1[CH:34]=[CH:33][C:22]([CH:23]=[C:24]([C:29]([O:31][CH3:32])=[O:30])[C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[O:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=[C:9]1[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][O:18][C:19]2[CH:20]=[CH:21][C:22]([CH:23]=[C:24]([C:25]([O:27][CH3:28])=[O:26])[C:29]([O:31][CH3:32])=[O:30])=[CH:33][CH:34]=2)=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 103565Dimethyl ((4-hydroxyphenyl)methylene)malonateHCID 14074166p-(Benzoxazoyl)benzyl Chloride

Product 1

HCID 21315311Dimethyl 4-[4-(2-benzoxazolyl)benzyloxy]-benzylidenemalonateYield 41%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 0.1 mole 2-(4-chloromethylphenyl)benzoxazole (C) and 0.1 mole dimethyl 4-hydroxybenzylidenemalonate (D) in 300 ml. 2-butanone containing 100 g. potassium carbonate was refluxed for 18 hours and poured onto 1,000 g. ice/water. Filtration, washing with water and recrystallization from methyl cellosolve/isopropyl alcohol gave a 41% yield of the light tan crystalline product II. ##STR5##

Workup

  1. additionpoured onto 1,000 g
  2. filtrationFiltration
  3. washwashing with water and recrystallization from methyl cellosolve/isopropyl alcohol

Sources & evidence

ORD record
ord-656514d7db8c4f6ead7126615e24ee8a
Source dataset
uspto-grants-1978_02
Patent number
US04075162

Reaction notes

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