Dimethylamine → 2-((Dimethylamino)methyl)phenol

HRID 65553Notes

Reaction equation

HRID 65553 reaction equation
[CH:1](=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH3:10][NH:11][CH3:12].[H][H]>O.[Pd]>[CH3:10][N:11]([CH2:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4])[CH3:12]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 6998SalicylaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 328972-((Dimethylamino)methyl)phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

2-Dimethylaminomethyl phenol was prepared by the method of S. Cavitt, "J. Org. Chem.", 27, 1211 (1962). 61.0 gm salicylaldehyde, 127 gm 25% by wt dimethylamine in water and 1.2 gm 10% by wt palladium on charcoal are placed in a pressure bottle of a Parr hydrogenator and hydrogenated until 41.7 lbs of hydrogen are taken up. The experiment is repeated and reaction mixtures combined. The catalyst is filtered off and the filtrate made acidic (pH 2), extracted with ether, and the ether discarded. The aqueous phase is adjusted to pH 8 with NaOH and extracted with ether. The aqueous phase is adjusted to pH 9 with NaOH and extracted with ether. The ether extracts are combined, dried over MgSO4, filtered, and evaporated on a rotating evaporator. There results 111.7 gm of an orange liquid (Percent crude yield - 75). This is fractionated at reduced pressure. The product is collected at 60°-63° C. at 0.5 mm to provide 99.1 gm of a yellow liquid (Percent yield - 65).

Workup

  1. customreaction mixtures
  2. filtrationThe catalyst is filtered off
  3. extractionextracted with ether
  4. extractionextracted with ether
  5. extractionextracted with ether
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated on a rotating evaporator

Sources & evidence

ORD record
ord-8e8da3eb997a43448f875a03d0e34de2
Source dataset
uspto-grants-1978_12
Patent number
US04128429

Reaction notes

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