Water → 4-(2-Methoxy-4-nitrophenyl)but-3-en-2-ol

HRID 1916365Notes

Reaction equation

HRID 1916365 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[CH:12]=[CH:13][C:14](=[O:16])[CH3:15].[BH4-].[Na+].O>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[CH:12]=[CH:13][CH:14]([OH:16])[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 67066682CID 67066682

Product 1

HCID 670666784-(2-Methoxy-4-nitrophenyl)but-3-en-2-olYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 4-(2-methoxy-4-nitrophenyl)but-3-en-2-one (12.2 g; 55.2 mmol) in 150 mL of ethanol at rt was added NaBH4 (2.30 g; 60.7 mmol) over 5 minutes. The suspension was stirred at rt for 1 h, diluted with 1M NaHPO4 (˜60 mL) followed by water (100 mL) and concentrated under reduced pressure to remove ethanol. After extracting the aqueous residue with CH2Cl2, the organic layer was washed with water and brine, dried over anhydrous MgSO4, filtered. Concentration of the filtrate under reduced pressure afforded 12.3 g (100%) of the title compound as a dark, red gum. HPLC (Method #1) 3.68 min retention time, (50%); MS (ES): m/z 206 [M−OH]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove ethanol
  3. extractionAfter extracting the aqueous residue with CH2Cl2
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-95b891da4ff24113b652ae356b2a3bd9
Source dataset
uspto-grants-2013_12
Patent number
US08618115B2

Reaction notes

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