Acetone → CID 67066682

HRID 1916364Notes

Reaction equation

HRID 1916364 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[OH-].[Na+].Cl.[CH3:17][C:18]([CH3:20])=[O:19]>O>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:4]=1[CH:5]=[CH:17][C:18](=[O:19])[CH3:20]

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 27595992-Methoxy-4-nitrobenzaldehyde

Product 1

HCID 67066682CID 67066682Yield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of 2-methoxy-4-nitrobenzaldehyde (10.0 g; 55.2 mmol) in 11 mL of water and 11 mL of acetone at 65° C. was added a 1% solution of NaOH (13.8 mL) over 30 minutes. The mixture was heated at 65° C. for 2 h, cooled in an ice bath and neutralized with 10% HCl. A solid precipitated which was filtered, washed with water and dried under vacuum to afford 12.2 g (100%) of the title compound as a reddish-brown solid. HPLC (Method #1) 2.48 min retention time, (80%); MS (ES): m/z 222 [M+H]+.

Workup

  1. temperaturecooled in an ice bath
  2. customA solid precipitated which
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-816c0413d5804e47abaf958c10469d68
Source dataset
uspto-grants-2013_12
Patent number
US08618115B2

Reaction notes

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