2-Methylbenzenesulfonic acid → HCID 53796187, compound

HRID 439580Notes

Reaction equation

HRID 439580 reaction equation
[Cl:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([N+:15]([O-:17])=[O:16])[CH:8]=1)[C:3]([OH:5])=[O:4].[C:18]1(C)C(S(O)(=O)=O)=CC=C[CH:23]=1>C(O)C>[Cl:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([N+:15]([O-:17])=[O:16])[CH:8]=1)[C:3]([O:5][CH2:18][CH3:23])=[O:4]

Participants

4

Reactant 2

HCID 69252-Methylbenzenesulfonic acidHCID 53755901HCID 53755901, compound

Product 1

HCID 53796187HCID 53796187, compoundYield 710.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a ethanol solution of (S)-2-chloro-3-(4-methoxy-3-nitrophenyl)propionicacid (4.46 g) was added p toluenesulfonicacid (0.38 g) and heated under reflux for 5 hours.After cooled it down, the solvent was evaporated in vacuo. Theresultant suspension solution was extracted by ethyl acetate (50 ml×3).After the ethyl acetate layer was washed with saturated brine,dried over anhydrous sodium sulfate. The solvent was evaporated invacuo, the resultant crude product was purified by silica gel columnchromatography, and eluted with mixture of hexane or ethylacetate (4:1, v/v). The fractions containing the desired productwere combined and evaporated in vacuo to obtain ethyl (S)-2-chloro-3-(4-methoxy-3-nitrophenyl)propionate(4.51 g)

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter cooled it down
  4. customthe solvent was evaporated in vacuo
  5. extractionTheresultant suspension solution was extracted by ethyl acetate (50 ml×3).After the ethyl acetate layer
  6. washwas washed with saturated brine,dried over anhydrous sodium sulfate
  7. customThe solvent was evaporated invacuo
  8. customthe resultant crude product was purified by silica gel columnchromatography
  9. washeluted with mixture of hexane or ethylacetate (4:1
  10. additionThe fractions containing the
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-ebfa5cad61ec49e0b54aea154f684560
Source dataset
uspto-grants-1996_05
Patent number
US05514773

Reaction notes

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