2-Nitrophenol → Benzyl 2-nitrophenyl ether

HRID 1198518Notes

Reaction equation

HRID 1198518 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:11]([O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 69472-NitrophenolHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 736266Benzyl 2-nitrophenyl ether

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred mixture of 2-nitrophenol (13.9 g, 0.10 mol), benzyl bromide (12.0 ml, 0.10 mol) and anhydrous potassium carbonate (30 g, 0.22 mol) in acetone (200 ml) was heated under reflux for 16 hours, cooled, poured onto ice-dilute hydrochloric acid, and extracted with dichloromethane. The extract was dried and evaporated and the residue was crystallised from ether-hexane as pale crystals, m.p. <50° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. temperaturecooled
  4. additionpoured onto ice-dilute hydrochloric acid
  5. extractionextracted with dichloromethane
  6. customThe extract was dried
  7. customevaporated
  8. customthe residue was crystallised from ether-hexane as pale crystals, m.p. <50° C.

Sources & evidence

ORD record
ord-6d12826b9b214e8ea71a1210f46829e5
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

Loading…