Acetic Acid → HCID 54343451, compound

HRID 1381626Notes

Reaction equation

HRID 1381626 reaction equation
[CH3:1][C:2]1[C:3]([CH3:23])=[CH:4][C:5]2[O:9][C:8]([CH:10]=[CH:11][C:12]3[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=3)=[N:7][C:6]=2[CH:22]=1.C(O)(=O)C.S(=O)(=O)(O)O>O>[CH3:1][C:2]1[C:3]([CH3:23])=[CH:4][C:5]2[O:9][C:8]([CH:10]=[CH:11][C:12]3[CH:21]=[CH:20][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=3)=[N:7][C:6]=2[CH:22]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 102316Benzoic acid, 4-[2-(5,6-dimethyl-2-benzoxazolyl)ethenyl]-, methyl ester

Product 1

HCID 54343451HCID 54343451, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 3.0 g methyl 4-[(5,6-dimethyl-2-benzoxazolyl)vinyl]benzoate, 25 mL of acetic acid, 9.0 mL of concentrated sulfuric acid, and 7 mL of water is stirred and refluxed for three hours. The mixture is cooled and added to water. The product is collected by filtration, washed with water and air dried. The crude product is recrystallized from N,N-dimethylformamide to give 2.57 g of 4-[2-(5,6-dimethyl-2-benzoxazolyl)vinyl]benzoic acid, which melts at >300° C.

Workup

  1. temperaturerefluxed for three hours
  2. temperatureThe mixture is cooled
  3. filtrationThe product is collected by filtration
  4. washwashed with water and air
  5. customdried
  6. customThe crude product is recrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-9ce406e63caa46fe8fd5db9efff1d59a
Source dataset
uspto-grants-1989_02
Patent number
US04803241

Reaction notes

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