4-Nitrophenol → HCID 21250449, compound

HRID 1953292Notes

Reaction equation

HRID 1953292 reaction equation
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.N1[CH:16]=[CH:15]C=CC=1.Cl[C:18]([O:20]C(Cl)C)=[O:19].C(Cl)[Cl:25]>>[Cl:25][CH:15]([C:4]1[CH:5]=[C:6]([N+:7]([O-:9])=[O:8])[CH:1]=[CH:2][C:3]=1[O:10][C:18](=[O:19])[OH:20])[CH3:16]

Participants

5

Reactant 4

HCID 9804-NitrophenolHCID 1049PyridineHCID 6344DichloromethaneHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 21250449HCID 21250449, compound

Procedure

To a solution of 12.6 g (90 mmol) of p-nitrophenol in 300 ml methylene chloride and 7.2 g (91 mmol) of pyridine, 14.2 g (99 mmol) of 1-chloroethyl chloroformate are added dropwise at -10° C. The solution is stirred for 72 hours at ambient temperature and then extracted with water and 0.5% sodium hydroxide solution. The combined organic extracts are dried and concentrated by evaporation. The residue is chromatographed on aluminium oxide and eluted with methylene chloride. The combined fractions are concentrated by evaporation, triturated with petroleum ether and suction filtered.

Workup

  1. extractionextracted with water and 0.5% sodium hydroxide solution
  2. customThe combined organic extracts are dried
  3. concentrationconcentrated by evaporation
  4. customThe residue is chromatographed on aluminium oxide
  5. washeluted with methylene chloride
  6. concentrationThe combined fractions are concentrated by evaporation
  7. customtriturated with petroleum ether and suction
  8. filtrationfiltered

Sources & evidence

ORD record
ord-1f278cce02a44c7199c60e65541e586d
Source dataset
uspto-grants-2000_09
Patent number
US06114532

Reaction notes

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