Phenol → (R)-3-(1-Aminoethyl)phenol
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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]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](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.
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