Methane → 4-Amino-3-ethyl-5-methylphenol

HRID 1900539Notes

Reaction equation

HRID 1900539 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

HCID 297MethaneHCID 13307544HCID 13307544, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 233692554-Amino-3-ethyl-5-methylphenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

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

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. 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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