Sodium Hydroxide → 4-((1R)-1-Aminoethyl)phenol

Temperature

85 °C

(R)-1-(4-tert-Butoxyphenyl)ethylamine (89.4 g, 0.463 mol) was dissolved in 10% hydrochloric acid (200 ml) and heated to 85° C. At approx. 80° C., vigorous gas evolution set in. The mixture was stirred at 85° C. for another three hours, after which the gas evolution had stopped. The pale yellow mixture was allowed to cool to room temperature and then 20% NaOH was added dropwise up to a pH of 10.2. The deprotected phenol precipitated out overnight in the form of a pale yellow powder. It was filtered off with suction and dried in a drying cabinet overnight. For purification, the crude product was digested with tert-butyl methyl ether (200 ml). The suspension was filtered and the filter residue was dried again under reduced pressure. 51.3 g (63%) of (R)-4-(1-aminoethyl)phenol were obtained in the form of a pale yellow powder.

1. customAt approx. 80° C.
2. temperatureto cool to room temperature
3. customThe deprotected phenol precipitated out overnight in the form of a pale yellow powder
4. filtrationIt was filtered off with suction
5. customdried in a drying cabinet overnight
6. customFor purification
7. filtrationThe suspension was filtered
8. customthe filter residue was dried again under reduced pressure

ORD record

ord-726e863d8176456ca1b1439a13ec52bd

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07968328B2