Ethanol → Aniline

HRID 1249257Notes

Reaction equation

HRID 1249257 reaction equation
[CH2:1]([OH:3])[CH3:2].[N+:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([O-])=O.[CH3:13][OH:14]>>[C:7]1([NH:4][C:13](=[O:14])[O:3][CH2:1][CH3:2])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH2:4][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH:1](=[N:4][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].[CH2:1]([NH:4][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]

Participants

7

Reactant 3

HCID 702EthanolHCID 887MethanolHCID 7416Nitrobenzene

Product 4

HCID 6115AnilineHCID 7591Ethyl N-phenylcarbamateHCID 7670N-EthylanilineHCID 95796N-Ethylideneaniline

Procedure

The procedure was the same as for Example 1 with the exception that ethanol was substituted for methanol on an equal volume basis. Complete conversion of the nitrobenzene occurred in 4.5 hours at 160° C. and yielded 0.007 mole ethyl N-phenylcarbamate, 0.066 mole aniline, 0.004 mole ethylidene aniline, and 0.002 mole N-ethyl aniline. The balance (0.021 mole) was converted to higher molecular weight products derived from aniline.

Sources & evidence

ORD record
ord-52e124886b6440d1930d86865a2807af
Source dataset
uspto-grants-1986_12
Patent number
US04629804

Reaction notes

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