Ethanol → Aniline

HRID 1249258Notes

Reaction equation

HRID 1249258 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

Participants

5

Reactant 3

HCID 702EthanolHCID 887MethanolHCID 7416Nitrobenzene

Product 2

HCID 6115AnilineHCID 7591Ethyl N-phenylcarbamate

Procedure

The procedure was the same as for Example 2 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 0.014 mole ethyl N-phenylcarbamate, and 0.058 mole additional aniline (0.108 mole total aniline). The balance (0.023 mole) appeared as by-products derived from aniline. It is thus clear that the selectivity of the ruthenium catalyzed conversion of nitrobenzene and methanol to methyl N-phenylcarbamate is higher than the selectivity of the corresponding conversion of nitrobenzene and ethanol to ethyl N-phenylcarbamate even when aniline is added in order to improve the selectivity.

Sources & evidence

ORD record
ord-e2c27a1c03ca47d8b5e8ec729f86e02e
Source dataset
uspto-grants-1986_12
Patent number
US04629804

Reaction notes

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