Methanol → HCID 11063366, compound

HRID 1506951Notes

Reaction equation

HRID 1506951 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=[O:7].O=P(Cl)(Cl)Cl.[CH3:18]O>>[CH3:18][O:7][C:6](=[O:8])/[CH:5]=[CH:4]/[C:3]1[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=1[Cl:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 195673-(2-Chlorophenyl)acrylic acidHCID 24813Phosphorus oxychloride

Product 1

HCID 11063366HCID 11063366, compound

Procedure

To a 250 ml round-bottomed flask, 2-Chlorocinnamic acid (25 g, 136.9 mmol) and MeOH(56 ml) were added. POCl3 (1.27 ml, 13.6 mmol) was added dropwise. The reaction mixture was stirred under reflux for 3˜4 h. The reaction mixture was cooled to room temperature, quenched with 1N NaOH solution. The mixture was extracted by EtOAc and washed with H2O. The aqueous layer was further extracted with EtOAc. The combined organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated under vacuum. (26.98 g, 85˜97%)

Workup

  1. temperatureunder reflux for 3˜4 h
  2. customquenched with 1N NaOH solution
  3. extractionThe mixture was extracted by EtOAc
  4. washwashed with H2O
  5. extractionThe aqueous layer was further extracted with EtOAc
  6. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-03c1c67fb03d496aa591c85b9f555e1b
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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