Phenol → alpha-Hydroxy-beta-Phenoxy-N-(1-Methylethyl)Benzenepropanamide

Phenol (3.0 g.) was converted into its sodium salt by dissolving in a freshly prepared sodium methoxide-methanol solution (0.7 g. of metallic sodium in 50 ml. of absolute methanol), and subsequent evaporation of the excess methanol under reduced pressure on a rotary evaporator. The solid residue was dissolved in acetonitrile (250 ml.) by stirring with 18-crown-6 (0.9 g.) for 30 minutes at room temperature. N-(1-methylethyl)-3-phenyl-2-oxiranecarboxamide (6.16 g.) was added to the solution, and the resulting mixture was heated under reflux for 6 hours. After cooling to room temperature, it was filtered. The filtrate was evaporated on a rotary evaporator under reduced pressure to give a resinous material. Water (ca. 200 ml.) was added to the residue, and allowed to stand at room temperature. The white precipitate thus separated was collected on a filter and washed with water. The filter residue was dried in air, then recrystallized from ethanol, giving 2.5 g. of product, m.p. 166°-168°.

1. temperaturethe resulting mixture was heated
2. temperatureunder reflux for 6 hours
3. filtrationit was filtered
4. customThe filtrate was evaporated on a rotary evaporator under reduced pressure
5. customto give a resinous material
6. customto stand at room temperature
7. customThe white precipitate thus separated
8. customwas collected on
9. filtrationa filter
10. washwashed with water
11. customThe filter residue was dried in air
12. customrecrystallized from ethanol
13. customgiving 2.5 g

ORD record

ord-b94c7c4f3f3345489167438486243d79

Source dataset

uspto-grants-1982_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04341718