Hydrochloric Acid → Aniline, p-(decyloxy)-

HRID 902827Notes

Reaction equation

HRID 902827 reaction equation
Cl.[CH2:2]([O:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].O.O.[Sn](Cl)Cl>C(O)C>[CH2:2]([O:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 61436Stannous chloride dihydrateHCID 141653Decyl 4-nitrophenyl ether

Product 1

HCID 38359Aniline, p-(decyloxy)-Yield 92.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethanol (100 ml) and concentrated hydrochloric acid (5 ml) were added to the 4-decyloxynitrobenzene 2 (28.3 g, 101 mmol) thus obtained to prepare a solution which was then cooled in an ice bath. A hydrochloric acid solution of tin(II) chloride dihydrate (101.3 g, 450 mmol/HCl 50 ml) was added thereto. The mixture was stirred at room temperature for about 2 hr and was then stirred with heating at 60° C. for about 30 min. After the completion of the reaction, the resultant precipitate was collected by filtration. A 3 N aqueous sodium hydroxide solution was added to the collected precipitate, followed by extraction with ether. The filtrate was concentrated, and a 3 N aqueous sodium hydroxide solution was then added to the concentrate. The mixture was extracted with ether. The extract was washed with water, was then dried over sodium sulfate, and was concentrated to give 4-decyloxyaniline 3 as a reddish orange liquid (23.4 g, 92.7%).

Workup

  1. customthus obtained
  2. customto prepare a solution which
  3. temperaturewas then cooled in an ice bath
  4. stirringwas then stirred
  5. temperaturewith heating at 60° C. for about 30 min
  6. customAfter the completion of the reaction
  7. filtrationthe resultant precipitate was collected by filtration
  8. additionA 3 N aqueous sodium hydroxide solution was added to the collected precipitate
  9. extractionfollowed by extraction with ether
  10. concentrationThe filtrate was concentrated
  11. additiona 3 N aqueous sodium hydroxide solution was then added to the concentrate
  12. extractionThe mixture was extracted with ether
  13. washThe extract was washed with water
  14. dry with materialwas then dried over sodium sulfate
  15. concentrationwas concentrated

Sources & evidence

ORD record
ord-78ff2b5dbf334e6a9708552366fad8d3
Source dataset
uspto-grants-2008_04
Patent number
US07365359B2

Reaction notes

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