Hydrochloric Acid → HCID 18357677, compound

HRID 428034Notes

Reaction equation

HRID 428034 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([CH3:25])([CH2:22][CH:23]=[CH2:24])[C:17]([O:19]CC)=[O:18])=[N:2]1.[OH-].[K+].Cl>COCCO>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([CH3:25])([CH2:22][CH:23]=[CH2:24])[C:17]([OH:19])=[O:18])=[N:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 18357535HCID 18357535, compound

Product 1

HCID 18357677HCID 18357677, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

To a solution of 0.75 g of ethyl 2-[2-(1,2-benzisoxazol-3-yl)-phenyl]-2-methyl-4-pentenoate in 10 ml of 2-methoxyethanol was added 5 ml of 10M potassium hydroxide solution. The solution was refluxed overnight then cooled to room temperature and poured onto ice. This aqueous solution was acidified with 5M hydrochloric acid and extracted with three 100 ml portions of ether. The extracts were evaporated and azeotroped with toluene. Flash chromatography of the residue, eluting with 0 to 10% methanol in methylene chloride, afforded 0.52 g of 2-[2-(1,2-benzisoxazol-3-yl)-phenyl]-2-methyl-4-pentenoic acid as a gum, 1H NMR (400 MHz; CDCl3) δH 1.52 (Me).

Workup

  1. temperatureThe solution was refluxed overnight
  2. additionpoured onto ice
  3. extractionextracted with three 100 ml portions of ether
  4. customThe extracts were evaporated
  5. customazeotroped with toluene
  6. washFlash chromatography of the residue, eluting with 0 to 10% methanol in methylene chloride

Sources & evidence

ORD record
ord-ba67972a9d424dc9b38236df6600524c
Source dataset
uspto-grants-2001_11
Patent number
US06313139B1

Reaction notes

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