Benzyl Chloride → 5-Benzyloxy-2-chloro-nitrobenzene

HRID 1031660Notes

Reaction equation

HRID 1031660 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].[H-].[Na+].[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(OCC)(=O)C>CN(C)C=O>[CH2:14]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 691274-Chloro-3-nitrophenol

Product 1

HCID 110436225-Benzyloxy-2-chloro-nitrobenzeneYield 59.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.0 g of 4-chloro-3-nitrophenol was dissolved in 15 ml of N,N-dimethylformamide. Thereto was added 490 mg of sodium hydride (purity: 60%) in 10 minutes at 5°-10° C. Then, 1.53 g of benzyl chloride was added dropwise in 10 minutes. Stirring was conducted for 1 hour at 70° C. The reaction mixture was introduced into a mixture of 50 ml of ice water and 50 ml of ethyl acetate. The resulting organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was washed with n-hexane and then mixed with a mixture of diisopropyl ether and n-hexane. The resulting crystal was collected by filtration to obtain 1.8 g (yield: 59.4%) of 4-benzyloxy-2-nitro-chlorobenzene having a melting point of 50°-50.5° C.

Workup

  1. customThe resulting organic layer was separated
  2. washwashed with water
  3. dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. washThe residue was washed with n-hexane
  6. additionmixed with a mixture of diisopropyl ether and n-hexane
  7. filtrationThe resulting crystal was collected by filtration

Sources & evidence

ORD record
ord-5d00b3daeb1d4d6fb4db1a9e91acb15a
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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