Sodium Hydroxide → 4-(allyloxy)aniline

HRID 1030261Notes

Reaction equation

HRID 1030261 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH:10]=[CH2:11])=[CH:6][CH:5]=1)([O-])=O.[OH-].[Na+]>Cl>[NH2:1][C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH:10]=[CH2:11])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 220100Allyl p-nitrophenyl ether

Product 1

HCID 65042044-(allyloxy)anilineYield 81%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
55 °C

Procedure

To 3-[(4-nitro)phenoxy]-1-propene, prepared by the process of Example 1, Step 1, (12.65 g, 70.67 mmol) in concentrated HCl (85 mL) at 0° C., was slowly added stannous chloride (48 g, 212 mmol). After stirring for 20 minutes at 55° C., the mixture was cooled to 0° C. and carefully basified with 50% NaOH. The cloudy mixture was extracted with ether. The organic phase was decolorized (charcoal), dried (MgSO4), and concentrated to afford product (8.50 g, 81%) as a yellow oil which was used directly in the next step.

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. extractionThe cloudy mixture was extracted with ether
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9e6d76d6ef874988993396d14f410167
Source dataset
uspto-grants-1992_04
Patent number
US05104892

Reaction notes

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