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Acetic Acid → N-(2-isopropoxybenzyl)-2-phenoxyaniline

HRID 2271190
Notes
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Reaction equation

HRID 2271190 reaction equation
[CH:1]([O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=O)([CH3:3])[CH3:2].[CH:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[C:25]([NH2:26])=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:15][CH:14]=1.[BH4-].[Na+].C(O)(=O)C>CO>[CH:1]([O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7][NH:26][C:25]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:19][C:16]1[CH:15]=[CH:14][CH:13]=[CH:18][CH:17]=1)([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 75899Benzenamine, 2-phenoxy-HCID 2500782-(Propan-2-yloxy)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 18407213N-(2-isopropoxybenzyl)-2-phenoxyanilineYield 79.6%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

To a solution of 1.64 g of 2-isopropoxybenzaldehyde in 10 ml of methanol was added 1.85 g of 2-aminodiphenyl ether, and then the mixture was stirred at room temperature for 30 minutes and cooled on ice-water. To the cooled reaction solution was gradually added 1.50 g of sodium borohydride, followed by stirring under ice-cooling for 30 minutes and then at room temperature for 30 minutes. An aqueous acetic acid solution (1.5 ml of acetic acid-30 ml of water) was added dropwise to the reaction solution, followed by stirring at room temperature for 10 minutes. After extraction with ethyl acetate, the extract was washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate-hexane=1:25) to give 2.65 g of N-(2-isopropoxybenzyl)-2-phenoxyaniline as an oil.

Workup

  1. temperaturecooled on ice-water
  2. customTo the cooled reaction solution
  3. stirringby stirring under ice-
  4. temperaturecooling for 30 minutes
  5. waitat room temperature for 30 minutes
  6. stirringby stirring at room temperature for 10 minutes
  7. extractionAfter extraction with ethyl acetate
  8. washthe extract was washed with a saturated aqueous sodium bicarbonate solution
  9. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate
  10. customAfter removal of the drying agent
  11. filtrationby filtration
  12. concentrationthe filtrate was concentrated under reduced pressure
  13. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate-hexane=1:25)

Sources & evidence

ORD record
ord-0f1ada75563e4fbbaa1e74af953a88e5
Source dataset
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06333358B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes