Phenol → (R)-3-(1-Aminoethyl)phenol

HRID 2425850Notes

Reaction equation

HRID 2425850 reaction equation
C([O:5][C:6]1[CH:7]=[C:8]([C@H:12]([NH2:14])[CH3:13])[CH:9]=[CH:10][CH:11]=1)(C)(C)C.S(=O)(=O)(O)O.[OH-].[Na+].C1(O)C=CC=CC=1>O>[NH2:14][C@@H:12]([C:8]1[CH:7]=[C:6]([OH:5])[CH:11]=[CH:10][CH:9]=1)[CH3:13]

Participants

6

Reactant 4

HCID 996PhenolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 55264960(R)-1-(3-tert-butoxyphenyl)ethylamine

Product 1

HCID 40427058(R)-3-(1-Aminoethyl)phenolYield 73.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

(R)-1-(3-tert-Butoxyphenyl)ethylamine (5 g, 25.9 mmol) was suspended in water (10 ml) and admixed with 38% sulfuric acid up to a pH of 1. The mixture was heated to 85° C. and stirred at this temperature for another three hours, after which the gas evolution had stopped. The colorless mixture was allowed to cool to room temperature and then 20% NaOH was added dropwise up to a pH of 9.1, whereupon the protected phenol precipitated out in the form of a white powder. This was filtered off with suction and dried overnight in a drying cabinet. 2.6 g (73%) of (R)-3-(1-aminoethyl)phenol were obtained in the form of a pale yellow powder.

Workup

  1. temperatureto cool to room temperature
  2. customprecipitated out in the form of a white powder
  3. filtrationThis was filtered off with suction
  4. customdried overnight in a drying cabinet

Sources & evidence

ORD record
ord-70d459fb8ea4446e989f1298ad023cde
Source dataset
uspto-grants-2011_06
Patent number
US07968328B2

Reaction notes

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