Sodium Hydroxide → HCID 54029401, compound

HRID 1603946Notes

Reaction equation

HRID 1603946 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](C(OC)=O)([CH2:15][CH:16]=[CH2:17])[C:11]([O:13]C)=[O:12])=[CH:5][C:4]=1[O:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[OH-].[Na+]>CO.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([CH2:15][CH:16]=[CH2:17])[C:11]([OH:13])=[O:12])=[CH:5][C:4]=1[O:22][CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54055058HCID 54055058, compound

Product 1

HCID 54029401HCID 54029401, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of the methyl 3-[4-methoxy-3-(2-phenylethoxy) phenyl]-2-methoxycarbonyl-2-(2-propen-1-yl)propionate (7.50 g) in 75 ml of methanol, 0.73 g of sodium hydroxide in 1.1 ml of water was added and refluxed by heating for 30 hours under stirring. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in 61 ml of aqueous solution of 3 N sodium hydroxide. The solution was refluxed by heating for 11 hours under stirring. The reaction solution cooled to room temperature was washed with diethyl ether. Then, concentrated hydrochloric acid was added thereto to make the solution acidic. The resultant solution was extracted with dichloromethane and dried over anhydrous magnesium sulfate. The drying agent was separated by filtration and the filtrate was concentrated under reduced pressure. The residue was stirred at 140-150° C. for 4 hours under heating to obtain 6.21 g of crude 3-[4-methoxy-3-(2-phenylethoxy)phenyl]-2-(2-propen-1-yl) propionic acid. This crude compound was used in the subsequent step without purification.

Workup

  1. temperaturerefluxed
  2. temperatureby heating for 30 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in 61 ml of aqueous solution of 3 N sodium hydroxide
  5. temperatureThe solution was refluxed
  6. temperatureby heating for 11 hours
  7. stirringunder stirring
  8. washwas washed with diethyl ether
  9. additionThen, concentrated hydrochloric acid was added
  10. extractionThe resultant solution was extracted with dichloromethane
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe drying agent was separated by filtration
  13. concentrationthe filtrate was concentrated under reduced pressure
  14. stirringThe residue was stirred at 140-150° C. for 4 hours
  15. temperatureunder heating

Sources & evidence

ORD record
ord-725f3e47f2bd4a7f91cd21e76a9d08fe
Source dataset
uspto-grants-1999_11
Patent number
US05990151

Reaction notes

Loading…