Hydrochloric Acid → 1-(4-Methyl-3-nitrophenyl)ethan-1-ol

HRID 2410000Notes

Reaction equation

HRID 2410000 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[BH4-].[Na+].Cl.O>C(O)C.O1CCCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 792463'-Nitro-4'-methylacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 434983221-(4-Methyl-3-nitrophenyl)ethan-1-olYield 96.9%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of 1-(4-methyl-3-nitrophenyl)ethan-1-one (2.00 g) in ethanol/tetrahydrofuran (15 mL/7.5 mL) was added sodium borohydride (211 mg), and the mixture was stirred at room temperature for 10 minutes. To the reaction mixture were added 0.5 mol/L hydrochloric acid and water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain the title compound (1.96 g). 1H-NMR (CDCl3) δ ppm: 1.52 (3H, d, J=6.5 Hz), 1.84-1.95 (1H, m), 2.59 (3H, s), 4.91-5.02 (1H, m), 7.32 (1H, d, J=7.9 Hz), 7.52 (1H, dd, J=1.8, 7.9 Hz), 7.99 (1H, d, J=1.8 Hz).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-af36a9945cba487986fc7b4893b59d1b
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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