Ethanol → HCID 58424985, compound

HRID 2409446Notes

Reaction equation

HRID 2409446 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:6]([OH:8])=[O:7].S(Cl)(Cl)=O.[CH2:19](O)[CH3:20]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:6]([O:8][CH2:19][CH3:20])=[O:7]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 53002123-Methoxy-5-nitrobenzoic acid

Product 1

HCID 58424985HCID 58424985, compoundYield 85.6%

Procedure

The compound (5.33 g, 27.0 mmol) prepared in step 1 was dissolved in absolute ethanol (55.0 ml), added dropwise with thionyl chloride (2.96 ml, 40.55 mmol) at 0° C. The resulting mixture was refluxed for 6 hours. After completion, the reaction mixture was concentrated under reduced pressure and mixed with sodium bicarbonate aqueous solution. The mixture was extracted with dichloromethan, dried over anhydrous magnesium sulfate, and concentrated to dryness. The residue was then purified by flash column chromatography (dichloromethane:hexane=4:1) to obtain the title compound (5.1 g, yield: 85.6%, ivory solid).

Workup

  1. temperatureThe resulting mixture was refluxed for 6 hours
  2. concentrationAfter completion, the reaction mixture was concentrated under reduced pressure
  3. additionmixed with sodium bicarbonate aqueous solution
  4. extractionThe mixture was extracted with dichloromethan
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated to dryness
  7. customThe residue was then purified by flash column chromatography (dichloromethane:hexane=4:1)

Sources & evidence

ORD record
ord-58939c9f7446408ab52f1b6405e7cb91
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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