Hydrochloric Acid → 4-(2-Aminoethoxy)phenol--hydrogen chloride (1/1)

HRID 339796Notes

Reaction equation

HRID 339796 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[ClH:12].[H][H]>CCO.[Pd]>[ClH:12].[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 30165354-(2-Aminoethoxy)phenolHCID 178418361HCID 178418361, compound

Product 1

HCID 221541064-(2-Aminoethoxy)phenol--hydrogen chloride (1/1)Yield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-(2-Aminoethyloxy)-phenol. In a Parr bottle the product from Preparation 8, Step 1. (10.7 g, 44.7 mmol) was dissolved in absolute EtOH (100 mL). The solution was treated with 37% HCl (9 g) and 10% Pd/C (1.8 g). The reaction mixture was de-aerated, then charged with hydrogen (initial pressure: 50 pso H2) and shaken for 16 h. The mixture was filtered and the filtrate was concentrated in vacuo to afford 4-(2-aminoethoxy)-phenol hydrochloride salt (7.22 g, 85%) as a beige solid. This material was used without further purification.

Workup

  1. customIn a Parr bottle the product from Preparation 8, Step 1
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1a436ad9b3884dd4a7bb6ea6f154cf3e
Source dataset
uspto-grants-2014_11
Patent number
US08895568B2

Reaction notes

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