Allyl bromide → Ethyl 2-(3-nitro-4-allyloxyphenyl)propionate

HRID 328165Notes

Reaction equation

HRID 328165 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][C:9]=1[OH:10])([O-:3])=[O:2].[CH2:18](Br)[CH:19]=[CH2:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][C:9]=1[O:10][CH2:20][CH:19]=[CH2:18])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 21444155Ethyl 2-(4-hydroxy-3-nitrophenyl)propanoate

Product 1

HCID 21444159Ethyl 2-(3-nitro-4-allyloxyphenyl)propionate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2.39g of ethyl 2-(3-nitro-4-hydroxyphenyl)propionate, 1.45g of allylbromide and 1.65g of potassium carbonate in 20ml of acetone was refluxed for 4 hours. After cooling, the solvent was distilled under reduced pressure. The residue was dissolved in ethyl acetate and washed with water. After the solution was dried over magnesium sulfate, the solvent was distilled off. The thus obtained oily substance was purified by means of silica gel chromatography, to give the object compound in a yield of 2.51g (90%).

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperatureAfter cooling
  3. distillationthe solvent was distilled under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialAfter the solution was dried over magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customThe thus obtained oily substance was purified by means of silica gel chromatography
  9. customto give the object compound in a yield of 2.51g (90%)

Sources & evidence

ORD record
ord-db37a75043164c6b8b4aa3f1463faeb9
Source dataset
uspto-grants-1977_04
Patent number
US04016193

Reaction notes

Loading…