Isoeugenol → HCID 86079729, compound

HRID 1680542Notes

Reaction equation

HRID 1680542 reaction equation
[C:1]1([O:11][CH3:12])[C:2](=[CH:4][CH:5]=[C:6]([CH:10]=1)[CH:7]=[CH:8][CH3:9])[OH:3].[C:13](OC(=O)C)(=[O:15])[CH3:14]>N1C=CC=CC=1>[C:13]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH3:9])[CH:10]=[C:1]([O:11][CH3:12])[C:2]=1[OH:3])(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 7338IsoeugenolHCID 7918Acetic Anhydride

Product 1

HCID 86079729HCID 86079729, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of isoeugenol (344 g., 2.1 moles) in 420 ml. of pyridine under nitrogen atmosphere is added 428 ml. of acetic anhydride over a period of 30 minutes. The resulting solution is stirred at room temperature overnight followed by treatment with ice-water (1400 ml.). After stirring for three hours, the resulting precipitate is filtered, washed with water (3×500 ml.) and dried in vacuo to give 381.7 g. of crude product. Acetyl isoeugenol (269 g., 62%) is obtained from washing the crude product with n-hexane.

Workup

  1. stirringAfter stirring for three hours
  2. filtrationthe resulting precipitate is filtered
  3. washwashed with water (3×500 ml.)
  4. customdried in vacuo
  5. customto give 381.7 g

Sources & evidence

ORD record
ord-c454ebe31f7f402e82663a4121862bfd
Source dataset
uspto-grants-1981_06
Patent number
US04273943

Reaction notes

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