Hydrochloric Acid → 1-[4-(4-Amino-benzyloxy)-2-hydroxy-3-propyl-phenyl]-ethanone

HRID 2267018Notes

Reaction equation

HRID 2267018 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)[CH:5]=[CH:4][C:3]=1[C:22](=[O:24])[CH3:23].Cl>O1CCCC1>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][O:11][C:6]2[CH:5]=[CH:4][C:3]([C:22](=[O:24])[CH3:23])=[C:2]([OH:1])[C:7]=2[CH2:8][CH2:9][CH3:10])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68430465HCID 68430465, compound

Product 1

HCID 684314821-[4-(4-Amino-benzyloxy)-2-hydroxy-3-propyl-phenyl]-ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1-[2-Hydroxy-4-(4-nitro-benzyloxy)-3-propyl-phenyl]-ethanone (1.0 g, 3.0 mmol) in tetrahydrofuran (13 mL) is added concentrated hydrochloric acid (2.7 mL) and stannous chloride dihydrate (2.2 g, 9.9 mmol). The reaction mixture is stirred at room temperature overnight. The reaction mixture is quenched into saturated aqueous NH4Cl (100 mL). The resulting emulsion is filtered and the filtrate extracted with ethyl acetate (3×100 mL). The combined organic layers are washed with brine, dried over sodium sulfatesodium sulfate, and concentrated to provide the title compound in crude form (980 mg,). LC-MS (m/z): 298 (M−1).

Workup

  1. customThe reaction mixture is quenched into saturated aqueous NH4Cl (100 mL)
  2. filtrationThe resulting emulsion is filtered
  3. extractionthe filtrate extracted with ethyl acetate (3×100 mL)
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over sodium sulfatesodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e55d81a746c84154a753034c564e0d11
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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