Dimethylamine → 2-[(Dimethylamino)methyl]-4-(trifluoromethoxy)phenol
Reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH2:13]=O.O.[CH3:16][NH:17][CH3:18]>>[OH:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:9][C:8]=1[CH2:16][N:17]([CH3:13])[CH3:18]Participants
Conditions
- Temperature
- 3 °C
Procedure
130 g of 4-trifluoromethoxyphenol are initially charged in 97 ml of 40% aqueous dimethylamine solution and cooled to 3° C. At 0-5° C., 66 ml of 37% aqueous formaldehyde solution are added dropwise within 45 min. The mixture is kept at 5-10° C. for a further 2 hours and is subsequently stirred at room temperature for 19 hours. It is cooled again to 0° C., 4.9 ml of 40% aqueous dimethylamine solution are added and 3.3 ml of 37% aqueous formaldehyde solution are subsequently added dropwise. The mixture is stirred at room temperature for a further 3 hours. The mixture is admixed with 100 ml of water. The organic phase is removed, the aqueous phase is extracted twice with dichloromethane, the combined organic phases are dried and the solvent is distilled off under reduced pressure. The crude product is subsequently fractionally distilled under reduced pressure. 118 g (69% of theory) of a light yellow liquid having a boiling point of 110-112° C. at 18 mbar were obtained.
Workup
- temperatureIt is cooled again to 0° C.
- stirringThe mixture is stirred at room temperature for a further 3 hours
- customThe organic phase is removed
- extractionthe aqueous phase is extracted twice with dichloromethane
- customthe combined organic phases are dried
- distillationthe solvent is distilled off under reduced pressure
- distillationThe crude product is subsequently fractionally distilled under reduced pressure
- customwere obtained
Sources & evidence
- ORD record
- ord-3111e731c0144dea8e0a812f295fe090
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06903239B2
Reaction notes
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