Methane → 4-Amino-3-ethyl-5-methylphenol
Reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([OH:12])[CH:6]=[C:7]([CH3:11])[C:8]=1[N:9]=O)[CH3:2].C.[H][H]>O1CCCC1.[Pd]>[CH2:1]([C:3]1[CH:4]=[C:5]([OH:12])[CH:6]=[C:7]([CH3:11])[C:8]=1[NH2:9])[CH3:2]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
88.7 g (537.6 mmol) of the 3-ethyl-4-nitroso-5-methylphenol prepared in stage 1 are catalytically hydrogenated in 1 liter of tetrahydrofuran (THF) with molecular hydrogen under 5 bar at 20°-25° C. 10 g of 5% palladium on active charcoal (Pd-C) are used as catalyst. The hydrogen uptake is 77% of theory. The catalyst is filtered off, the filtrate is evaporated and the residue is recrystallised from methanol. Yield 51.2 g (63.2% of theory); melting point 167°-170° C.
Workup
- filtrationThe catalyst is filtered off
- customthe filtrate is evaporated
- customthe residue is recrystallised from methanol
Sources & evidence
- ORD record
- ord-5851858540074e85a26bd5c30f17dc8d
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05576188
Reaction notes
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