4-Benzyloxyaniline → Ethylene Oxide

HRID 716833Notes

Reaction equation

HRID 716833 reaction equation
[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Fe].CC(O)=O.[Pd]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:13])=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:9]1[O:8][CH2:15]1

Participants

5

Reactant 1

HCID 228604-Benzyloxyaniline

Product 2

HCID 6354Ethylene OxideHCID 228604-Benzyloxyaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 45051903EisenazetatCatalyst

Procedure

Phenol N-mustard is synthesized by to known procedures with modification. Scheme 4 shows the synthetic route for phenol mustard. Treatment of 4-nitrophenol (20) with benzyl chloride or 4-fluoro-1-nitrobenzene (22) with benzyl alcohol in the presence of base (such as NaOH, KOH, Na2CO3, K2CO3 or organic base) gives compound 21, which is converted into 4-benzyloxyaniline (23) by reduction (Fe/CH3COOH or Pd/C, H2). Treatment of 23 with ethylene oxide affords 4-N,N-bis(2-hydroxyethyl)aminophenyl benzyl ether 24.37

Sources & evidence

ORD record
ord-9017b2522c8e4f81a72a1055ccaaa2d7
Source dataset
uspto-grants-2015_11
Patent number
US09193687B2

Reaction notes

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