Acetic Acid → 2-Chloro-5-nitro-alpha-methylcinnamaldehyde

HRID 2254904Notes

Reaction equation

HRID 2254904 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:5]=1[CH:6]=O.[CH:15](=[O:18])[CH2:16][CH3:17].C(O)(=O)C>O.CO>[Cl:3][C:4]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:5]=1[CH:6]=[C:16]([CH3:17])[CH:15]=[O:18]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 14798Sodium HydroxideHCID 729332-Chloro-5-nitrobenzaldehyde

Product 1

HCID 544427022-Chloro-5-nitro-alpha-methylcinnamaldehydeYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4 g of NaOH dissolved in 20 ml of water were added to a suspension of 185.5 g (1 mole) of 2-chloro-5-nitrobenzaldehyde in 500 ml of methanol, after which 70 g (1.2 moles) of propionaldehyde were added dropwise while cooling to 10°-15° C. The mixture was stirred for 2 days at room temperature and then neutralized with glacial acetic acid, and the precipitated solid was isolated by filtration under suction, washed with water and dried at 50° C. under reduced pressure to give the product of melting point 99°-102° C. in 78% yield.

Workup

  1. temperaturewhile cooling to 10°-15° C
  2. customthe precipitated solid was isolated by filtration under suction
  3. washwashed with water
  4. customdried at 50° C. under reduced pressure
  5. customto give the product of melting point 99°-102° C. in 78% yield

Sources & evidence

ORD record
ord-f576bd349f2c4e2fba4bdf327b13634a
Source dataset
uspto-grants-1993_08
Patent number
US05237089

Reaction notes

Loading…