Hydrochloric Acid → 3-Aminostyrene

HRID 2248064Notes

Reaction equation

HRID 2248064 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[CH:5]=1)=O.[BH4-].[Na+].Cl>C(O)(C)C>[NH2:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[CH:2]=[CH2:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 74173'-AminoacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 42600413-Aminostyrene

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

135 g (1 mol) of 3-aminoacetophenone are suspended in 1,000 ml of isopropanol, and 19 g (0.5 mol) of sodium borohydride are slowly added. The reaction mixture is stirred at room temperature for 48 hours and then brought to a pH of 5 with concentrated hydrochloric acid, while cooling with ice. The salt which is precipitated is filtered off with suction, and the slightly reddish solution is concentrated on a rotary evaporator under a water pump vacuum. The desired 1-(3-aminophenyl)ethanol crystallizes overnight in the cold, is filtered off with suction and dried.

Workup

  1. temperaturewhile cooling with ice
  2. customThe salt which is precipitated
  3. filtrationis filtered off with suction
  4. concentrationthe slightly reddish solution is concentrated on a rotary evaporator under a water pump vacuum
  5. customThe desired 1-(3-aminophenyl)ethanol crystallizes overnight in the cold,
  6. filtrationis filtered off with suction
  7. customdried

Sources & evidence

ORD record
ord-d83db2edef0542c0ab39c980b5eb555a
Source dataset
uspto-grants-1991_08
Patent number
US05037961

Reaction notes

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