Benzyl Alcohol → HCID 58945262, compound

HRID 659997Notes

Reaction equation

HRID 659997 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:30](O)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[N:38](C(OCC)=O)=NC(OCC)=O>ClCCl>[CH2:30]([O:10][C:5]1[CH:6]=[CH:7][C:8]([NH2:38])=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 69472-NitrophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 58945262HCID 58945262, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-amino, 2-nitrophenol (1 mmol), triphenyl phosphine (1.2 mmol) and benzyl alcohol (1.2 mmol) in dry dichloromethane (5 ml) at ambient temperature, under a nitrogen atmosphere, was added a solution of diethyl azodicarboxylate (1.2 mmol) in dry dichloromethane (2 ml). The resultant mixture was stirred at ambient temperature for 18 hr. Evaporation under reduced pressure afforded a gum that was purified by column chromatography (SiO2; diethyl ether) to give 4-benzyloxy-3-nitro-aniline, yield 85%.

Workup

  1. customEvaporation under reduced pressure
  2. customafforded a gum that
  3. customwas purified by column chromatography (SiO2; diethyl ether)

Sources & evidence

ORD record
ord-f95605f2b8264babbf897fb9b40bd2dc
Source dataset
uspto-grants-2011_12
Patent number
US08084457B2

Reaction notes

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