Water → HCID 68927469, compound

HRID 1866131Notes

Reaction equation

HRID 1866131 reaction equation
[NH:1]([C:5]1[CH:11]=[CH:10][C:8]([OH:9])=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3].[C:12]([O:15][C:16]1[CH:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[C:24](Cl)=[O:25])=[CH:18][C:17]=1[O:27][CH3:28])(=[O:14])[CH3:13].O>N1C=CC=CC=1.CC(C)=O>[C:2]([NH:1][C:5]1[CH:11]=[CH:10][C:8]([O:9][C:24](=[O:25])/[CH:23]=[CH:22]/[C:19]2[CH:20]=[CH:21][C:16]([O:15][C:12](=[O:14])[CH3:13])=[C:17]([O:27][CH3:28])[CH:18]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:4]

Participants

6

Reactant 3

HCID 962WaterHCID 1983AcetaminophenHCID 10858041HCID 10858041, compound

Product 1

HCID 68927469HCID 68927469, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1049PyridineSolvent

Procedure

To a solution of paracetamol (2.56 g, 16.92 mmoles) in pyridine (20 ml) cooled in an ice bath trans-3-[4-acetyloxy-3-methoxyphenyl]-2-propenoyl chloride (4.31 g, 16.92 mmoles) dissolved in acetone (45 ml) is dropped. The mixture is maintained under stirring in ice for 3 hours then it is poured into water (300 ml) and the precipitate is filtered and triturated with hexane to give trans-3-[4-acetyloxy-3-methoxyphenyl]-2-propenoic acid 4-(acetylamino)phenyl ester (4.38 g) as an orange solid. M.p. 246-250° C. Yield 70%.

Workup

  1. additionis dropped
  2. temperatureThe mixture is maintained
  3. filtrationthe precipitate is filtered
  4. customtriturated with hexane

Sources & evidence

ORD record
ord-b4a7ca0729ec4de19604822903cb3a77
Source dataset
uspto-grants-2009_12
Patent number
US07629368B2

Reaction notes

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