Hydrochloric Acid → 2-Acetyl-4-methoxyphenyl 4-nitrobenzoate

HRID 215675

Reaction equation

HRID 215675 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([OH:12])=[C:7]([C:9](=[O:11])[CH3:10])[CH:8]=1.[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14].Cl>N1C=CC=CC=1>[C:9]([C:7]1[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[O:12][C:20](=[O:21])[C:19]1[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:24][CH:23]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 85024-Nitrobenzoyl chlorideHCID 697141-(2-Hydroxy-5-methoxyphenyl)ethan-1-one

Product 1

HCID 7760892-Acetyl-4-methoxyphenyl 4-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5′-methoxy-2′-hydroxyacetophenone (1.5 g, 9.03 mmol) was added to a pyridine solution (20 ml) that contained 4-nitrobenzoyl chloride (1.72 g, 9.26 mmol) in an ice bath. The obtained mixture was reacted at room temperature for 30 minutes, and the reaction solution was then poured into 1 N hydrochloric acid under cooling on ice. The obtained mixture was intensively stirred. The obtained precipitate was collected by filtration, and the filtrate was then washed with purified water, so as to obtain a product of interest, 4-nitrobenzoic acid 2-acetyl-4-methoxyphenyl ester (compound 21). Yield: 2.49 g (yield constant: 87.4%)

Workup

  1. customThe obtained mixture was reacted at room temperature for 30 minutes
  2. temperatureunder cooling on ice
  3. filtrationThe obtained precipitate was collected by filtration
  4. washthe filtrate was then washed with purified water

Sources & evidence

ORD record
ord-0fda36c95d0a4a968ebfdb678629eeee
Source dataset
uspto-grants-2012_06
Patent number
US08192717B2

Linked notes

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