4-Chlorophenol → 4-chloro-2-[(dimethylamino)methyl]phenol

HRID 1598314Notes

Reaction equation

HRID 1598314 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][N:10]([CH2:12]N(C)C)[CH3:11]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:9][N:10]([CH3:12])[CH3:11])[CH:3]=1

Participants

4

Reactant 2

HCID 46844-ChlorophenolHCID 5829N,N,N',N'-Tetramethylmethanediamine

Product 1

HCID 3081744-chloro-2-[(dimethylamino)methyl]phenol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-chlorophenol (25.72 g), N,N,N',N'-tetramethyldiaminomethane (27.2 ml) and 1,4-dioxane (250 ml) was heated on a steam bath for 16 hours. The mixture was evaporated to dryness and the residue was dissolved in 2M hydrochloric acid, washed with dichloromethane, basified with concentrated sodium hydroxide solution and extracted with dichloromethane to give an oil which was distilled to give 4-chloro-2-(dimethylaminomethyl)phenol, b.p. 90°-97° C. at 0.26 mbar.

Workup

  1. customThe mixture was evaporated to dryness
  2. dissolutionthe residue was dissolved in 2M hydrochloric acid
  3. washwashed with dichloromethane
  4. extractionextracted with dichloromethane
  5. customto give an oil which
  6. distillationwas distilled

Sources & evidence

ORD record
ord-40c9f55c12a6447c8b08ad3388b2195d
Source dataset
uspto-grants-1998_04
Patent number
US05736568

Reaction notes

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