Reaction #2286277

Reaction equation

2,6-dimethyl phenol

dimethylamine

dimethylamine

formaldehyde

formaldehyde

hydrochloric acid

→

4-dimethylaminomethyl-2,6-dimethyl-phenol

Yield 46.0%

Solvents

ethanol

water

water

water

Conditions

Workup

1. 1
   TemperatureThe reaction was heated
2. 2
   Temperatureto reflux for 12 h
3. 3
   ExtractionThe water layer was extracted with diethyl ether (2×150 mL)
4. 4
   workup.ADDITIONThe aqueous layer was brought to pH=8 by the addition of a 1N aqueous sodium hydroxide solution
5. 5
   Temperaturecooled to 0° C. in an ice bath
6. 6
   Extractionwas extracted with diethyl ether (3×200 mL)
7. 7
   WashThe organics were washed with a saturated aqueous sodium chloride solution
8. 8
   Dryingdried with magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Concentrationconcentrated under vacuum
11. 11
    OtherThe resulting oil was dried under high vacuum overnight

Procedure

A solution of 2,6-dimethyl phenol (20 g, 0.163 mol) in ethanol (100 mL) at room temperature was treated with dimethylamine (19 mL of a 40% solution of dimethylamine in water, 0.163 mol) followed by formaldehyde (13.5 mL of a 37% solution of formaldehyde in water, 0.163 mol). The reaction was heated to reflux for 12 h. The reaction mixture was cooled to 0° C. in an ice bath, diluted with water (100 mL) and brought to pH=5 with a 1N aqueous hydrochloric acid solution. The water layer was extracted with diethyl ether (2×150 mL). The aqueous layer was brought to pH=8 by the addition of a 1N aqueous sodium hydroxide solution, cooled to 0° C. in an ice bath and was extracted with diethyl ether (3×200 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 4-dimethylaminomethyl-2,6-dimethyl-phenol as an off-white solid (13.42 g, 46%); EI(+)-HRMS m/z calcd for C11H17NO (M+) 179.1310, found 179.1308. Molecular Weight=179.2642; Exact Mass=179.1310

Source