Methanol → HCID 53767292, compound

HRID 2298463Notes

Reaction equation

HRID 2298463 reaction equation
[C:1]1([C:7](=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19]O>>[CH3:19][O:9][C:8](=[O:10])[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18]

Participants

3

Reactant 2

HCID 887MethanolHCID 348318HCID 348318, compound

Product 1

HCID 53767292HCID 53767292, compound

Procedure

αPhenyl-2-chlorocinnamic acid (26.29 g (0.102 M) was dissolved in methanol (300 cc). Anhydrous HCl was bubbled through the reaction mixture with stirring for 15 minutes. The reaction mixture was refluxed for 2 hours, then HCl was bubbled through the reaction mixture for another 15 minutes. The reaction was stirred at reflux overnight. The methanol was removed in vacuo and the residue taken up in ether. The ether solution was washed with H2O, saturated NaHCO3 solution, and brine. It was then dried over MgSO4. The ether solution was concentrated in vacuo to yield an oil that quickly solidified to yield 27.13 g of product, mp 67-69° C.

Workup

  1. customAnhydrous HCl was bubbled through the reaction mixture
  2. temperatureThe reaction mixture was refluxed for 2 hours
  3. customHCl was bubbled through the reaction mixture for another 15 minutes
  4. stirringThe reaction was stirred
  5. temperatureat reflux overnight
  6. customThe methanol was removed in vacuo
  7. washThe ether solution was washed with H2O, saturated NaHCO3 solution, and brine
  8. dry with materialIt was then dried over MgSO4
  9. concentrationThe ether solution was concentrated in vacuo
  10. customto yield an oil that

Sources & evidence

ORD record
ord-5f68ab2276a54272b30f3ee088e4b6bf
Source dataset
uspto-grants-2002_12
Patent number
US06492531B1

Reaction notes

Loading…