Hydrochloric Acid → 5-(Aminomethyl)-2-propoxyphenol

HRID 2236439Notes

Reaction equation

HRID 2236439 reaction equation
CO[N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH3:14])=[C:7]([OH:15])[CH:6]=1.Cl>C(O)C.[Pd]>[NH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH3:14])=[C:7]([OH:15])[CH:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 748285453-hydroxy-4-propoxybenzaldehyde O-methyloxime

Product 1

HCID 219043645-(Aminomethyl)-2-propoxyphenolYield 74.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

An amount of 3-hydroxy-4-propoxybenzaldehyde O-methyloxime (150 mg, 0.83 mmol) is dissolved in ethanol (4 mL). Then hydrogen chloride (0.600 mL) is added, followed by 10% Pd/C (15.0 mg). After hydrogenation at 35 psi for 3 h, the solution is filtered through Celite and evaporated to dryness. The residue is recrystallized from ethyl acetate to give 112 mg of crude product as a white solid. MS (ESI) m/z 182.3 (M+1)

Workup

  1. filtrationthe solution is filtered through Celite
  2. customevaporated to dryness
  3. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0f95f2d2b85747909290080c3d2fcef2
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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