4-Nitrophenol → 3-(Acetylthio)propanoic acid p-nitrophenyl ester

HRID 1706011Notes

Reaction equation

HRID 1706011 reaction equation
[C:1]([S:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].[CH:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[C:12](O)[CH:11]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C>[N+:16]([C:15]1[CH:10]=[CH:11][C:12]([O:8][C:7](=[O:9])[CH2:6][CH2:5][S:4][C:1](=[O:3])[CH3:2])=[CH:13][CH:14]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 2627193-(Acetylthio)propionic Acid

Product 1

HCID 538511433-(Acetylthio)propanoic acid p-nitrophenyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred ice cold solution of ethyl acetate (75 ml.) containing 3-(acetylthio)propanoic acid (7.4 g. 50 mmol.) and p-nitrophenol (8.4 g., 60 mmol.) dicyclohexylcarbodiimide (10.3 g., 50 mmol.) is added in portions. After thirty minutes, the ice bath is removed and the solution stirred at room temperature overnight. The precipitated dicyclohexylurea is filtered off, ethyl acetate evaporated, and the residue dissolved in ethanol. The 3-(acetylthio)propanoic acid p-nitrophenyl ester crystallizes out, yield 8.6 g. (63.7%), m.p. 71°-73°.

Workup

  1. additionis added in portions
  2. waitAfter thirty minutes
  3. customthe ice bath is removed
  4. filtrationThe precipitated dicyclohexylurea is filtered off
  5. customethyl acetate evaporated
  6. dissolutionthe residue dissolved in ethanol
  7. customThe 3-(acetylthio)propanoic acid p-nitrophenyl ester crystallizes out

Sources & evidence

ORD record
ord-1d27a3ccbc964b5797fa4920760fbb66
Source dataset
uspto-grants-1980_06
Patent number
US04206122

Reaction notes

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