Benzyl Alcohol → 4-Benzyloxy-3-chloronitrobenzene

HRID 1013913Notes

Reaction equation

HRID 1013913 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:5]=[C:6]([N+:11]([O-:13])=[O:12])[CH:7]=[CH:8][C:9]=1F.[CH2:14]([OH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(#N)C>[CH2:14]([O:21][C:9]1[CH:8]=[CH:7][C:6]([N+:11]([O-:13])=[O:12])=[CH:5][C:4]=1[Cl:3])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 14797Potassium HydroxideHCID 676882-Chloro-1-fluoro-4-nitrobenzene

Product 1

HCID 3085094-Benzyloxy-3-chloronitrobenzeneYield 75.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 15.43 g (0.275 moles) portion of solid (pellets) potassium hydroxide was added to a solution of 43.89 g (0.25 moles) of 3-chloro-4-fluoro nitrobenzene and 32.34 ml (33.79 grams, 0.373 moles) of benzyl alcohol in 220 ml of acetonitrile. The reaction was vigorously stirred with a mechanical stirrer overnight. The resulting solid was filtered. Concentration of the filtrate gave a second crop, which was also filtered. On standing more solid came out of this filtrate. This mixture was treated with ether, and the solid filtered. All solids were washed thoroughly with water, and combined to give 49.71 g of the title compound.

Workup

  1. filtrationThe resulting solid was filtered
  2. customConcentration of the filtrate gave a second crop, which
  3. filtrationwas also filtered
  4. additionThis mixture was treated with ether
  5. filtrationthe solid filtered
  6. washAll solids were washed thoroughly with water

Sources & evidence

ORD record
ord-58bfc3ed250047fbb65e5723ee1d678e
Source dataset
uspto-grants-2011_07
Patent number
US07982043B2

Reaction notes

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