Acetic Acid → HCID 19773533, compound

HRID 1614326Notes

Reaction equation

HRID 1614326 reaction equation
[C:1]([O:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)=O)(=O)[CH2:2][CH3:3].C([O-])(=O)C.[NH4+:20].C(O)(=O)C>O>[CH2:2]([C:1]1[O:5][CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[N:20]=1)[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517165Ammonium Acetate2×HCID 53859419HCID 53859419, compound

Product 1

HCID 19773533HCID 19773533, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6.2 parts of 2-(4-hydroxyphenyl)-2-oxoethyl propanoate, 2.7 parts of ammonium acetate and 52.5 parts of acetic acid was stirred for 6 hours at reflux temperature. An additional 2.7 parts of ammonium acetate were added and stirring was continued for 5 hours at reflux temperature and overnight at room temperature. The reaction mixture was poured into water and the precipitate was filtered off, yielding a first fraction of product. The aqueous layer was extracted with methylbenzene. The extract was dried, filtered and then combined with the first product fraction. The whole was dried, filtered and evaporated, yielding 3.8 parts (66.9%) of 4-(2-ethyl-4-oxazolyl)phenol (interm. 12).

Workup

  1. temperatureat reflux temperature
  2. stirringstirring
  3. waitwas continued for 5 hours
  4. filtrationthe precipitate was filtered off
  5. customyielding a first fraction of product
  6. extractionThe aqueous layer was extracted with methylbenzene
  7. customThe extract was dried
  8. filtrationfiltered
  9. customThe whole was dried
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-6c547e4c6532407dbdfb4a55ec56488d
Source dataset
uspto-grants-1993_03
Patent number
US05196535

Reaction notes

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