Sodium Hydroxide → HCID 15728712, compound

Temperature

45 °C

A mixture of 950 mg (3.9 mmol) of 2,2,4,4,7-pentamethyl-6-acetylchroman (Compound 53), 100 ml of 10% sodium hypochlorite solution, 10 ml of a solution of 1.52 g (38 mmol) of sodium hydroxide in water and 10 ml of dioxane was heated at 45° C. for 72 hours. The mixture was cooled to room temperature and washed with 2×25 ml of ether. The aqueous layer was then treated with sodium metabisulphite until it was negative to the potassium iodide-starch test. The aqueous layer was acidified to pH=2 with dilute H2SO4 and the mixture was then stored in the refrigerator for 48 hours. The mixture was extracted with 3×25 ml of ether. The ether extracts were then combined and washed successively with water and saturated NaCl solution and then dried (MgSO4). The solution was then filtered and the filtrate was concentrated in-vacuo to give the title compound as a white solid. PMR (CDCl3): & 1.34 (12H, s), 1.82 (2H, s), 2.53 (3H, s), 6.64 (1H, s), 8.03 (1 H, s).

1. temperatureThe mixture was cooled to room temperature
2. washwashed with 2×25 ml of ether
3. additionThe aqueous layer was then treated with sodium metabisulphite until it
4. extractionThe mixture was extracted with 3×25 ml of ether
5. washwashed successively with water and saturated NaCl solution
6. dry with materialdried (MgSO4)
7. filtrationThe solution was then filtered
8. concentrationthe filtrate was concentrated in-vacuo

ORD record

ord-2d80a10fbfe64de8a17b3d8b50180616

Source dataset

uspto-grants-1991_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05006550