2-Nitrophenol → HCID 23347822, compound

HRID 1855705Notes

Reaction equation

HRID 1855705 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]([O:13][CH2:14][CH2:15]Br)[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:11]([O:13][CH2:14][CH2:15][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[CH3:12]

Participants

5

Reactant 3

HCID 69472-NitrophenolHCID 11430Potassium CarbonateHCID 611412-Bromoethyl ethyl ether

Product 1

HCID 23347822HCID 23347822, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Nitrophenol (91.0 g., 0.65 mole), 2-bromoethyl ethyl ether (100.0 g., 0.65 mole), anhydrous potassium carbonate (9.0 g, 0.72 mole) and acetone (1 liter) were refluxed for 65 hours. The reaction mixture was filtered, and the acetone removed by rotary evaporation. The residue was partitioned between 200 ml. of dichloromethane and 100 ml. water. The organic phase was further washed with 200 ml. of 10% sodium hydroxide followed by 100 cc of water. The product (58.0 g) was obtained in 42% yield by a vacuum distillation (100°-120° C./0.5 mm).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe acetone removed by rotary evaporation
  3. customThe residue was partitioned between 200 ml
  4. washThe organic phase was further washed with 200 ml

Sources & evidence

ORD record
ord-5ae9805c480d42558b10e2b92dc71dfa
Source dataset
uspto-grants-1980_08
Patent number
US04216152

Reaction notes

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