Sodium Hydroxide → 4-Chloro-3-[(prop-2-en-1-yl)oxy]aniline

HRID 1638914Notes

Reaction equation

HRID 1638914 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:6]=1[Cl:14])[CH:2]=[CH2:3].[OH-].[Na+]>C(O)C>[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([CH:8]=[CH:7][C:6]=1[Cl:14])[NH2:11])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 128819301-(Allyloxy)-2-chloro-5-nitrobenzene

Product 1

HCID 544961134-Chloro-3-[(prop-2-en-1-yl)oxy]aniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 1.0 g of 3A and 5.3 g of stannous chloride dihydrate in 10 mL of absolute ethanol was heated for 1 hour. The resulting mixture was poured into 100 g of ice, then sufficient 10% aqueous sodium hydroxide solution was added, with stirring, to bring the pH of the mixture to 10. The mixture was extracted with ethyl acetate, then with ether. The combined extracts were washed with water, then brine, then dried (Na2SO4) and stripped of the solvents, to give 3-(allyloxy)-4-chloroaniline (3B), as a brown oil.

Workup

  1. temperaturewas heated for 1 hour
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe combined extracts were washed with water
  4. dry with materialbrine, then dried (Na2SO4)

Sources & evidence

ORD record
ord-2ecda020225e4baca61ee6a5acf98da0
Source dataset
uspto-grants-1989_11
Patent number
US04881967

Reaction notes

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