Acetone → 30625-99-1

HRID 1256084Notes

Reaction equation

HRID 1256084 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].O.[OH-].[Na+].[CH3:15][C:16]([CH3:18])=[O:17]>>[N+:1]([C:4]1[CH:5]=[C:6](/[CH:7]=[CH:15]/[C:16](=[O:17])[CH3:18])[CH:9]=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 180Acetone2×HCID 962WaterHCID 74493-NitrobenzaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 537450230625-99-1Yield 78%

Procedure

The mixture of 3-nitrobenzaldehyde (15.1 g, 0.1 mol), acetone (20 mL) and water (40 mL) was slowly added 5% aqueous NaOH (8 mL) from a dropping funnel at 40° C. After the reactant disappeared in TLC monitoring, acetone was removed under reduced pressure. The residue was extracted with ethyl acetate. The organic layer was separated, washed with brine, dried (Na2SO4) and concentrated to give the (E)-4-(3-nitrophenyl)but-3-en-2-one (15 g, 78% yield) as a yellow oil. 1H NMR: (400 MHz, CDCl3) δ 8.31 (t, 1H), 8.15 (t, 1H), 7.83 (d, 1H), 7.52 (t, 1H), 7.44 (d, 1H), 6.70 (d, 1H), 2.33 (s, 3H).

Workup

  1. customat 40° C
  2. customwas removed under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f39a157d65b34781ab20c291bca84a52
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

Loading…