反応 #2286284

反応方程式

formaldehyde

formaldehyde

2-chloro-6-methyl phenol

dimethyl amine

dimethylamine

→

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

収率 66.0%

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

収率 66.0%

溶媒

water

ethanol

water

反応条件

後処理

1. 1
   温度The reaction was heated
2. 2
   温度to reflux for 24 h
3. 3
   濃縮concentrated 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
   抽出The 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
   抽出was extracted with ethyl acetate (2×350 mL)
9. 9
   洗浄The organics were washed with a saturated aqueous sodium chloride solution
10. 10
    乾燥dried with magnesium sulfate
11. 11
    ろ過filtered
12. 12
    濃縮concentrated under vacuum
13. 13
    その他The resulting oil was dried under high vacuum overnight

実験手順

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

出典