Acetic Anhydride → HCID 57461443, compound

HRID 230780Notes

Reaction equation

HRID 230780 reaction equation
C(OC(=O)C)(=O)C.[N:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:15].[CH:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:20][CH:19]=1)=O.[OH-].[Na+]>O>[CH3:14][C:13]1[N:8]=[C:9](/[CH:15]=[CH:16]/[C:18]2[CH:19]=[CH:20][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:23]=2)[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 79372,6-LutidineHCID 14798Sodium HydroxideHCID 15294Methyl 4-Formylbenzoate

Product 1

HCID 57461443HCID 57461443, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An acetic anhydride solution (100 mL) of 2,6-lutidine (65 g) and methyl 4-formylbenzenecarboxylate (20 g) was stirred overnight at 180° C. The reaction solution was poured into water with ice, and aqueous 5 N sodium hydroxide solution was added thereto until it became alkaline. The resulting mixture was extracted with ethyl acetate, and the organic layer was dried with anhydrous magnesium sulfate. The solvent was evaporated off, and the resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1 to 4/1) to obtain the entitled compound (20.1 g).

Workup

  1. additionwas added
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  4. customThe solvent was evaporated off
  5. customthe resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1 to 4/1)

Sources & evidence

ORD record
ord-ce9e80fe1aca49acabc6720b1ba8337e
Source dataset
uspto-grants-2009_07
Patent number
US07566781B2

Reaction notes

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