반응 #1172209

반응 방정식

2,2,4,4,7-pentamethyl-6-acetylchroman

Compound 53

2,2,4,4,7-pentamethyl-6-acetylchroman

sodium hypochlorite

sodium hydroxide

→

title compound

2,2,4,4,7-Pentamethyl-6-carboxychroman

용매

water

dioxane

반응 조건

후처리

1. 1
   온도The mixture was cooled to room temperature
2. 2
   세척washed with 2×25 ml of ether
3. 3
   workup.ADDITIONThe aqueous layer was then treated with sodium metabisulphite until it
4. 4
   추출The mixture was extracted with 3×25 ml of ether
5. 5
   세척washed successively with water and saturated NaCl solution
6. 6
   건조dried (MgSO4)
7. 7
   여과The solution was then filtered
8. 8
   농축the filtrate was concentrated in-vacuo

실험 절차

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).

출처