Triethylamine → Veratryl alcohol

HRID 54665

Reaction equation

HRID 54665 reaction equation
Cl.NC[CH:4]([OH:15])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1.COC1C(OC)=CC=CC=1C=O.C(N(CC)CC)C.B.[Na]>CO>[CH3:14][O:13][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[O:11][CH3:12])[CH2:4][OH:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 665812,3-DimethoxybenzaldehydeHCID 128889092-Amino-1-(3,4-dimethoxyphenyl)ethan-1-ol hydrochlorideHCID 178418435HCID 178418435, compound

Product 1

HCID 7118Veratryl alcohol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.0 g of α-(aminomethyl)-3,4-dimethoxybenzyl alcohol hydrochloride was suspended in 5 ml of methanol, and after adding thereto 0.85 g of 2,3-dimethoxybenzaldehyde, 0.63 ml of triethylamine was added dropwise to the mixture while stirring at room temperature. The mixture was heated under reflux for 30 minutes, and 0.24 g of sodium boron hydride was added slowly to the mixture while stirring under ice cooling. After the foaming stopped, the mixture was concentrated. The residue was subjected to a separating procedure with chloroform and water, the chloroform layer was collected, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was recrystallized from ethyl acetate-n-hexane, giving 1.07 g of α-[[2,3-dimethoxybenzyl)amino]methyl]-3,4-dimethoxybenzyl alcohol, m.p. 96°-97° C.

Workup

  1. additionafter adding
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 30 minutes
  4. stirringwhile stirring under ice cooling
  5. concentrationthe mixture was concentrated
  6. customthe chloroform layer was collected
  7. washwashed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off
  10. customthe residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-3bcdb4656b234fc0b193760fcf8acf5b
Source dataset
uspto-grants-1997_04
Patent number
US05623074

Linked notes

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