Methyl 2-(4-hydroxy-3-nitrophenyl)acetate → Methyl 3-nitro-4-methallyloxyphenylacetate

HRID 328166Notes

Reaction equation

HRID 328166 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:7]=[CH:8][C:9]=1[OH:10])([O-:3])=[O:2].[C:16]1([CH3:30])[CH:21]=CC(S(OCC(=C)C)(=O)=O)=C[CH:17]=1.C[O-].[Na+]>CO>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:7]=[CH:8][C:9]=1[O:10][CH2:21][C:16](=[CH2:17])[CH3:30])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 1473109Methyl 2-(4-hydroxy-3-nitrophenyl)acetateHCID 10942334Sodium MethoxideHCID 10955266Methallyl p-toluenesulfonate

Product 1

HCID 21444153Methyl 3-nitro-4-methallyloxyphenylacetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2.11g of methyl 3-nitro-4-hydroxyphenylacetate, 2.27g of methallyl p-toluenesulfonate was refluxed for one hour in 60ml of methanol containing natrium methoxide (natrium 0.25g). The reaction mixture was concentrated under reduced pressure and ethyl acetate and water were added to the residue. The ethyl acetate layer was isolated, and washed with water. After the extract was dried over magnesium sulfate, the solvent was distilled off and the residue was recrystallied from methanol to give the object compound having m.p. 30°- 31.5° C in a yield of 1.98g (74%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and ethyl acetate and water
  2. additionwere added to the residue
  3. customThe ethyl acetate layer was isolated
  4. washwashed with water
  5. dry with materialAfter the extract was dried over magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customto give the object compound

Sources & evidence

ORD record
ord-f9aa89924d974250968d5ec5c1499168
Source dataset
uspto-grants-1977_04
Patent number
US04016193

Reaction notes

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