Ammonium Chloride → 1-Methoxy-2-phenyl-pent-4-en-2-ol

HRID 1046053

Reaction equation

HRID 1046053 reaction equation
[CH3:1][O:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[CH2:12]([Mg]Cl)[CH:13]=[CH2:14].[NH4+].[Cl-]>O1CCCC1>[CH3:1][O:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([OH:5])[CH2:14][CH:13]=[CH2:12]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 776982-Methoxy-1-phenylethanoneHCID 178418473HCID 178418473, compound

Product 1

HCID 596356791-Methoxy-2-phenyl-pent-4-en-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Methoxy-1-phenyl-ethanone (5.00 g) dissolved in tetrahydrofuran (50 mL) was added to 2 M allylmagnesium chloride in tetrahydrofuran (21 mL) at room temperature. The solution was stirred at room temperature for 3 h and then 10% aqueous NH4Cl solution (50 mL) was added. The resulting mixture was extracted with tert-butyl methyl ether (3×50 mL) and the combined extracts were washed with water (50 mL) and brine (50 mL). The solvent was evaporated to afford the title compound as a colorless oil. Yield: 6.40 g (quantitative). Mass spectrum (ESI+): m/z=175 [M+H−H2O]+

Workup

  1. extractionThe resulting mixture was extracted with tert-butyl methyl ether (3×50 mL)
  2. washthe combined extracts were washed with water (50 mL) and brine (50 mL)
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-7a5e474b18594953808533ab179c6bd3
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Linked notes

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