Benzyl Bromide → 4-(Benzyloxy)-2-methyl-1-nitrobenzene

HRID 2292489Notes

Reaction equation

HRID 2292489 reaction equation
[N+:1]([C:4]1[C:5]([CH3:11])=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)([O-:3])=[O:2].[OH-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCC>[CH2:14]([O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([CH3:11])[CH:6]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 174123-Methyl-4-nitrophenol

Product 1

HCID 2577204-(Benzyloxy)-2-methyl-1-nitrobenzene

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a solution of 4-nitro-m-cresol (100.0 g) in methylene chloride (1000 ml) was added a 1N aqueous solution of sodium hydroxide (1000 ml). To the resulting two-layer solution were added in turn benzyl bromide (170 ml) and tetra-n-butylammonium bromide (2.17 g) while stirring at room temperature. After stirring at room temperature overnight, the reaction solution was placed into a separating funnel to separate the organic layer from the aqueous layer. The aqueous layer was extracted with methylene chloride. The combined organic layer was washed with saturated saline, dried over magnesium sulfate and the solvent was distilled off to give a yellow oily substance. The solidified yellow oily substance was ground in hexane, filtered and dried. The resulting yellow powder was recrystallized from an ethyl acetate/hexane mixed solvent system to give the title compound (116.7 g).

Workup

  1. stirringAfter stirring at room temperature overnight
  2. customthe reaction solution was placed into a separating funnel
  3. customto separate the organic layer from the aqueous layer
  4. extractionThe aqueous layer was extracted with methylene chloride
  5. washThe combined organic layer was washed with saturated saline
  6. dry with materialdried over magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customto give a yellow oily substance
  9. filtrationfiltered
  10. customdried
  11. customThe resulting yellow powder was recrystallized from an ethyl acetate/hexane mixed solvent system

Sources & evidence

ORD record
ord-a149a3a217b94cb1a16464c3b4072ee7
Source dataset
uspto-grants-1997_11
Patent number
US05684003

Reaction notes

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