Sodium Carbonate → HCID 66808438, compound

HRID 607297Notes

Reaction equation

HRID 607297 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].Br[CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:14])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 11454(1-Bromoethyl)benzeneHCID 691274-Chloro-3-nitrophenol

Product 1

HCID 66808438HCID 66808438, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-chloro-3-nitro-phenol (2.0 g, 11.5 mmol), 1-bromoethyl-benzene (3.2 g, 17.3 mmol), sodium carbonate (1.80 g, 17.0 mmol) in acetone (20 ml) was heated at reflux for 18 hours. The reaction mixture was cooled, the solids filtered off and the filtrate concentrated to a thick syrup under vacuum. The residue was dissolved in ether (80 ml) and washed with water (20 ml) and 30% KOH solution (2×20 ml) and the solvent is concentrated under vacuum leaving an oily residue as the title compound (3.01 g, 94%).

Workup

  1. temperatureat reflux for 18 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe solids filtered off
  4. concentrationthe filtrate concentrated to a thick syrup under vacuum
  5. dissolutionThe residue was dissolved in ether (80 ml)
  6. washwashed with water (20 ml) and 30% KOH solution (2×20 ml)
  7. concentrationthe solvent is concentrated under vacuum

Sources & evidence

ORD record
ord-74b0e2f588344d9f81acc3a82840ad70
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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