Hydrogen Bromide → 3-(2-Amino-2-phenylethyl)phenol

HRID 1679430Notes

Reaction equation

HRID 1679430 reaction equation
Cl.C[O:3][C:4]1[CH:5]=[C:6]([CH2:10][CH:11]([NH2:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:8][CH:9]=1.Br>C(O)(=O)C>[OH:3][C:4]1[CH:5]=[C:6]([CH2:10][CH:11]([NH2:18])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 2039693368770-54-7

Product 1

HCID 124668273-(2-Amino-2-phenylethyl)phenolYield 79.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of dl-2-(3-methoxyphenyl)-1-phenylethylamine hydrochloride (11.3 g), 48% hydrobromic acid (100 ml) and glacial acetic acid (30 ml) is refluxed for 4 hours. After the reaction, the solvent is distilled off. To the residue is added water and the mixture is made alkaline with ammonia and extracted with chloroform. The chloroform layer is dried over anhydrous potassium carbonate and the solvent is distilled off. To the residue is added ether. The precipitated crystals are separated by filtration and recrystallized from ethanol-ethyl acetate to give the desired compound (7.3 g), melting point: 179°-181° C.

Workup

  1. temperatureis refluxed for 4 hours
  2. customAfter the reaction
  3. distillationthe solvent is distilled off
  4. additionTo the residue is added water
  5. extractionextracted with chloroform
  6. dry with materialThe chloroform layer is dried over anhydrous potassium carbonate
  7. distillationthe solvent is distilled off
  8. additionTo the residue is added ether
  9. customThe precipitated crystals are separated by filtration
  10. customrecrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-a5703008905a455f9b35d65b8f2a06bd
Source dataset
uspto-grants-1978_03
Patent number
US04080453

Reaction notes

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