Sodium Hydroxide → 99-67-2

HRID 1907064Notes

Reaction equation

HRID 1907064 reaction equation
C([O:3][C:4](=[O:12])[CH:5]([CH2:9][CH:10]=[CH2:11])[CH2:6][CH:7]=[CH2:8])C.[OH-].[Na+]>CO.O>[CH2:6]([CH:5]([CH2:9][CH:10]=[CH2:11])[C:4]([OH:12])=[O:3])[CH:7]=[CH2:8]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10877522Diallylacetic Acid Ethyl Ester

Product 1

HCID 1261050999-67-2Yield 54.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 2-allylpent-4-enoic acid ethyl ester (prepared above, 9.0 g, 54 mmol) in 50 mL of methanol and 2 mL of water was added sodium hydroxide (2.5 g, 63 mmol, available from EMD). The solution was stirred for 15 hours, then heated at reflux temperature for 2 hours. After cooling the reaction mixture to room temperature, solvent was removed at reduced pressure. To the residue were added 75 mL of diethyl ether and 10 mL of concentrated hydrochloric acid. The mixture was stirred at room temperature for 10 minutes, then the layers were separated and the diethyl ether layer was dried over magnesium sulfate. After filtration to remove the magnesium sulfate, solvent was removed at reduced pressure to leave 4.1 g of 2-allylpent-4-enoic acid as a colorless oil whose structure was confirmed by NMR analyses.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 2 hours
  3. customsolvent was removed at reduced pressure
  4. additionTo the residue were added 75 mL of diethyl ether and 10 mL of concentrated hydrochloric acid
  5. stirringThe mixture was stirred at room temperature for 10 minutes
  6. customthe layers were separated
  7. dry with materialthe diethyl ether layer was dried over magnesium sulfate
  8. filtrationAfter filtration
  9. customto remove the magnesium sulfate, solvent
  10. customwas removed at reduced pressure

Sources & evidence

ORD record
ord-534a07c08e2640db9a0d12b4b74efbf0
Source dataset
uspto-grants-2013_12
Patent number
US08597784B2

Reaction notes

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