4-Nitrobenzaldehyde → HCID 53784447, compound

HRID 1883505Notes

Reaction equation

HRID 1883505 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1.[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1)([O-:17])=[O:16].C(N(CC)CC)C.C(OC(=O)C)(=O)C>O>[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:13])([F:14])[F:1])[CH:4]=2)[C:10]([OH:12])=[O:11])=[CH:20][CH:19]=1)([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 676953-(Trifluoromethyl)benzeneacetic acid

Product 1

HCID 53784447HCID 53784447, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of (3-trifluoromethyl-phenyl)-acetic acid (7.5 g, 36.7 mmol), 4-nitro-benzaldehyde (5.55 g, 36.7 mmol), triethylamine (4.8 g, 47.8 mmol), and acetic anhydride (14.3 g, 140 mmol) was refluxed for 6 hours. The reaction mixture was poured in acidified water (sulfuric acid, pH 1) and extracted with ethyl acetetate. The organic layer was evaporated and the residue was stirred with sodium bicarbonate solution. The precipitate was sucked off and the filtrate extracted with ethyl acetate. The water was acidified with hydrochloric acid and the resulting oil extracted with ethyl acetate to give 9.9 g of the desired product (80% yield).

Workup

  1. extractionextracted with ethyl acetetate
  2. customThe organic layer was evaporated
  3. extractionthe filtrate extracted with ethyl acetate
  4. extractionthe resulting oil extracted with ethyl acetate

Sources & evidence

ORD record
ord-b97e35ceeb7d418a94419234432bffd6
Source dataset
uspto-grants-2004_07
Patent number
US06759420B1

Reaction notes

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