Resorcinol → m-Phenylene bis[2-(4-Methylphenyl)-5-benzoxazolecarboxylate]

HRID 437041Notes

Reaction equation

HRID 437041 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([C:17](Cl)=[O:18])=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[C:20]1([CH:27]=[CH:26][CH:25]=[C:23]([OH:24])[CH:22]=1)[OH:21].[OH-:28].[Na+]>C(Cl)(Cl)Cl.O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([C:17]([O:21][C:20]4[CH:27]=[CH:26][CH:25]=[C:23]([O:24][C:17]([C:14]5[CH:15]=[CH:16][C:10]6[O:9][C:8]([C:5]7[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=7)=[N:12][C:11]=6[CH:13]=5)=[O:28])[CH:22]=4)=[O:18])=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 5054ResorcinolHCID 14798Sodium HydroxideHCID 203909272-(4-Methylphenyl)-1,3-benzoxazole-5-carbonyl chloride

Product 1

HCID 21429976m-Phenylene bis[2-(4-Methylphenyl)-5-benzoxazolecarboxylate]

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 1c (5.42 g. 0.02 mole), resorcinol (1.10 g., 0.02 mole), and sodium hydroxide (0.8 g., 0.02 mole) was refluxed for 3 hours in a mixture of chloroform (50 ml.) and water (15 ml.). Upon cooling a solid separated between the layers which was filtered, air-dried, and amounted to 2.43 g. (42%) of 1f. UV (CH2CH2) λ max 306 nm (52,000), ε325 = 13,000.

Workup

  1. temperatureUpon cooling a solid
  2. customseparated between the layers which
  3. filtrationwas filtered
  4. customair-dried

Sources & evidence

ORD record
ord-910d45279aef43b4b82d080e152e6b3b
Source dataset
uspto-grants-1977_06
Patent number
US04029670

Reaction notes

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