반응 #2286284

반응 방정식

formaldehyde

formaldehyde

2-chloro-6-methyl phenol

dimethyl amine

dimethylamine

→

2-chloro-4-dimethylaminomethyl-6-methyl-phenol

수율 66.0%

2-Chloro-4-dimethylaminomethyl-6-methyl-phenol

수율 66.0%

용매

water

ethanol

water

반응 조건

후처리

1. 1
   온도The reaction was heated
2. 2
   온도to reflux for 24 h
3. 3
   농축concentrated under vacuum
4. 4
   workup.ADDITIONThe resulting oil was diluted with water (200 mL)
5. 5
   workup.ADDITIONacidified to pH=2 by addition of a 1N aqueous hydrochloric acid solution
6. 6
   추출The water layer was extracted with ethyl acetate (300 mL)
7. 7
   workup.ADDITIONThe water layer was made basic to pH=10 by the addition of a 1N aqueous sodium hydroxide solution
8. 8
   추출was extracted with ethyl acetate (2×350 mL)
9. 9
   세척The organics were washed with a saturated aqueous sodium chloride solution
10. 10
    건조dried with magnesium sulfate
11. 11
    여과filtered
12. 12
    농축concentrated under vacuum
13. 13
    기타The resulting oil was dried under high vacuum overnight

실험 절차

A solution of 2-chloro-6-methyl phenol (5.0 g, 0.035 mol) in ethanol (25 mL) at room temperature was treated with dimethyl amine (3.95 mL of a 40% solution of dimethylamine in water, 0.035 mol) followed by formaldehyde (2.85 mL of a 37% solution of formaldehyde in water, 0.035 mol). The reaction was heated to reflux for 24 h. At this time, the reaction mixture was cooled to room temperature and concentrated under vacuum. The resulting oil was diluted with water (200 mL) and acidified to pH=2 by addition of a 1N aqueous hydrochloric acid solution. The water layer was extracted with ethyl acetate (300 mL). The ethyl acetate layer was discarded. The water layer was made basic to pH=10 by the addition of a 1N aqueous sodium hydroxide solution and was extracted with ethyl acetate (2×350 mL). The organics were washed with a saturated aqueous sodium chloride solution, dried with magnesium sulfate, filtered and concentrated under vacuum. The resulting oil was dried under high vacuum overnight to afford 2-chloro-4-dimethylaminomethyl-6-methyl-phenol (2b) (4.62 g, 66%) as an off-white solid; EI(+)-HRMS m/z calcd for C10H14ClNO (M+) 199.0764, found 199.0767. Molecular Weight=199.6822; Exact Mass=199.0764

출처