3-Hydroxybenzaldehyde → 3-[(2,4,6-Trimethyl-benzylamino)-methyl]-phenol

HRID 658072Notes

Reaction equation

HRID 658072 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[CH3:10][C:11]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[C:12]=1[CH2:13][NH2:14].[BH4-].[Na+].Cl.C([O-])(O)=O.[Na+]>CO>[CH3:10][C:11]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[C:12]=1[CH2:13][NH:14][CH2:5][C:4]1[CH:3]=[C:2]([OH:1])[CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 5

HCID 1013-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 4584332,4,6-TrimethylbenzylamineHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride

Product 1

HCID 689821863-[(2,4,6-Trimethyl-benzylamino)-methyl]-phenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Hydroxy-benzaldehyde (1.22 g, 0.01 mol) and 2,4,6-trimethyl-benzylamine (1.19 g, 0.01 mol) were added to methanol (10 mL) and the resulting mixture was stirred overnight. Sodium borohydride (0.45 g, 0.012 mol) was then added, and stirring was continued one hour. The resulting mixture was acidified with 2N HCl and then neutralized with saturated aqueous NaHCO3 solution to yield a gummy solution. The gummy solution was extracted with EtOAc (3×100 mL). The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo to yield a white solid.

Workup

  1. stirringstirring
  2. waitwas continued one hour
  3. customto yield a gummy solution
  4. extractionThe gummy solution was extracted with EtOAc (3×100 mL)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto yield a white solid

Sources & evidence

ORD record
ord-be333cfe5a40457c91984a3e50d1a8c0
Source dataset
uspto-grants-2011_12
Patent number
US08076358B2

Reaction notes

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