Benzyl Alcohol → HCID 10854250, compound

HRID 322861Notes

Reaction equation

HRID 322861 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].F[C:12]1[CH:17]=[C:16](F)[CH:15]=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20]>CN(C)C=O>[CH2:1]([O:8][C:12]1[CH:17]=[C:16]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:15]=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 10854250HCID 10854250, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl alcohol (5.4 g) is added slowly to a stirred suspension of sodium hydride (2 g, 60% dispersion in mineral oil) in dry dimethylformamide (100 mL). The mixture is stirred for 30 minutes then 2,4-difluoronitrobenzene (3.2 g) is added in one portion. The resulting black solution is stirred at room temperature for 18 hours ,evaporated and the residue partitioned between ether (200 mL) and water (100 mL). The organic phase is washed thoroughly with water, dried and evaporated. The residue is triturated with hot ethanol (50 mL) and the mixture cooled in an ice-bath. The insoluble material is purified by filtration through a bed of silica eluting with a mixture of dichloromethane and petroleum ether, b.p.40-60° C., (1:1 v/v). The filtrate is evaporated and the solid crystallised from ethanol to give 2,4-dibenzyloxynitrobenzene (2.3 g) as a cream coloured solid, m.p. 101-103° C. [Elemental analysis:- C,71.4; H,5.07; N,4.09%. Calculated:- C,71.6; H,5.11; N,4.18%].

Workup

  1. stirringThe resulting black solution is stirred at room temperature for 18 hours
  2. customthe residue partitioned between ether (200 mL) and water (100 mL)
  3. washThe organic phase is washed thoroughly with water
  4. customdried
  5. customevaporated
  6. customThe residue is triturated with hot ethanol (50 mL)
  7. temperaturethe mixture cooled in an ice-bath
  8. filtrationThe insoluble material is purified by filtration through a bed of silica eluting with a mixture of dichloromethane and petroleum ether, b.p.40-60° C., (1:1 v/v)
  9. customThe filtrate is evaporated
  10. customthe solid crystallised from ethanol

Sources & evidence

ORD record
ord-84214eefd698495aa24e52a74f9908d7
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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