Reaktion #2286284

Reaktionsgleichung

formaldehyde

formaldehyde

2-chloro-6-methyl phenol

dimethyl amine

dimethylamine

→

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

Ausbeute 66.0%

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

Ausbeute 66.0%

Lösungsmittel

water

ethanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was heated
2. 2
   Temperaturto reflux for 24 h
3. 3
   Einengenconcentrated 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
   ExtraktionThe 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
   Extraktionwas extracted with ethyl acetate (2×350 mL)
9. 9
   WaschenThe organics were washed with a saturated aqueous sodium chloride solution
10. 10
    Trocknendried with magnesium sulfate
11. 11
    Filtrationfiltered
12. 12
    Einengenconcentrated under vacuum
13. 13
    SonstigeThe resulting oil was dried under high vacuum overnight

Vorschrift

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

Quelle