2-Nitrophenol → 2-[(2-nitrophenoxy)methyl]oxirane

HRID 262369Notes

Reaction equation

HRID 262369 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][CH:19]1[CH2:21][O:20]1>CC(=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:18][CH:19]1[CH2:21][O:20]1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 69472-NitrophenolHCID 7835EpichlorohydrinHCID 11430Potassium Carbonate

Product 1

HCID 2199222-[(2-nitrophenoxy)methyl]oxiraneYield 20%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 139 parts of 2-nitrophenol and 138 parts of potassium carbonate in 640 parts of 2-propanone are added dropwise 215 parts of 2-(chloromethyl)oxirane. Upon completion, stirring is continued for 2 days at reflux. The formed precipitate is filtered off and the filter-cake is washed with 2-propanone. The filtrate is evaporated. The residue is crystallized from a mixture of 2,2'-oxybispropane and petroleumether (1:1 by volume). The product is filtered off and dried, yielding 38 parts (20%) of 2-(2-nitrophenoxymethyl)oxirane; mp. 56° C.

Workup

  1. temperatureat reflux
  2. filtrationThe formed precipitate is filtered off
  3. washthe filter-cake is washed with 2-propanone
  4. customThe filtrate is evaporated
  5. customThe residue is crystallized from a mixture of 2,2'-oxybispropane and petroleumether (1:1 by volume)
  6. filtrationThe product is filtered off
  7. customdried

Sources & evidence

ORD record
ord-2323a7f0f3f541fdb528aaad862e63fd
Source dataset
uspto-grants-1979_05
Patent number
US04154738

Reaction notes

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