Sulfuric Acid → 4-[3-(3-Methylphenyl)propyl]aniline

HRID 330574Notes

Reaction equation

HRID 330574 reaction equation
S(=O)(=O)(O)O.[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15](/[CH:17]=[CH:18]/[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=2)=O)=[CH:11][CH:10]=1)([O-])=O.[H][H]>C(O)(=O)C.[Pd]>[CH3:25][C:21]1[CH:20]=[C:19]([CH2:18][CH2:17][CH2:15][C:12]2[CH:11]=[CH:10][C:9]([NH2:6])=[CH:14][CH:13]=2)[CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 5780399(E)-3-(3-methylphenyl)-1-(4-nitrophenyl)prop-2-en-1-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 141279284-[3-(3-Methylphenyl)propyl]anilineYield 103.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

46 g (0.47 mole) of concentrated sulfuric acid and 8 g of palladium on 80% active carbon are added to a solution of 130 g (0.49 mole) of E-(3-methylstyryl) 4-nitrophenyl ketone in 1.3 l of glacial acetic acid, and the mixture is saturated with nitrogen. Thereafter, hydrogen gas is passed into the stirred mixture under atmospheric pressure. After about 30 l of hydrogen has been absorbed, the mixture is heated to 50°-70° C. and hydrogenated until the theoretical amount of hydrogen (about 66 l) has been consumed. The mixture is filtered under suction over kieselguhr, the filtrate is evaporated to dryness and the residue is stirred with 1 l of ice water, 200 ml of 50% strength sodium hydroxide solution and 800 ml of methyl tert-butyl ether. The aqueous phase is washed with 3 times 250 ml of methyl tert-butyl ether, and the combined organic phases are washed once with 250 ml of water and once with 250 ml of saturated NaCl solution, dried over Na2SO4 and evaporated down under reduced pressure to give 114 g of a brown oil of boiling point 158°-163° C./0.3 mm, which is about 95% pure (corresponding to 98% of theory) according to the gas chromatogram.

Workup

  1. customAfter about 30 l of hydrogen has been absorbed
  2. temperaturethe mixture is heated to 50°-70° C.
  3. customhas been consumed
  4. filtrationThe mixture is filtered under suction over kieselguhr
  5. customthe filtrate is evaporated to dryness
  6. washThe aqueous phase is washed with 3 times 250 ml of methyl tert-butyl ether
  7. washthe combined organic phases are washed once with 250 ml of water and once with 250 ml of saturated NaCl solution
  8. dry with materialdried over Na2SO4
  9. customevaporated down under reduced pressure

Sources & evidence

ORD record
ord-d371bd99e9a544a5bca8bd9017d6caa7
Source dataset
uspto-grants-1990_01
Patent number
US04897425

Reaction notes

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