Tetrahydrofuran → 5-(2-Chloro-4-methoxy-phenyl)-penta-2,4-dienoic acid

HRID 597883Notes

Reaction equation

HRID 597883 reaction equation
C([O:3][C:4](=[O:18])[CH:5]=[CH:6][CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[Cl:17])C.C1COCC1.[OH-].[K+]>CO.O>[Cl:17][C:10]1[CH:11]=[C:12]([O:15][CH3:16])[CH:13]=[CH:14][C:9]=1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]([OH:18])=[O:3]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 724730985-(2-Chloro-4-methoxy-phenyl)-penta-2,4-dienoic acid ethyl ester

Product 1

HCID 724729395-(2-Chloro-4-methoxy-phenyl)-penta-2,4-dienoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The crude ester product was taken up in 200 mL each of methanol and THF and then cooled to 0° C. To this mixture was added a solution of KOH (19 g, 0.338 mol, 3 eq.) in 200 mL H2O. The mixture was stirred at room temperature for 1.5 hr and the organic solvent was evaporated. The aqueous layer was diluted with 300 mL H2O and washed with ether to remove the mineral oil. It was then cooled in an ice-bath and acidified with concentrated HCl to ˜pH 2. The thick precipitate was filtered and rinsed with water, then dried in a vacuum oven at 75° C. to provide 26.2 g of 5-(2-chloro-4-methoxy-phenyl)-penta-2,4-dienoic acid.

Workup

  1. customthe organic solvent was evaporated
  2. additionThe aqueous layer was diluted with 300 mL H2O
  3. washwashed with ether
  4. customto remove the mineral oil
  5. temperatureIt was then cooled in an ice-bath
  6. filtrationThe thick precipitate was filtered
  7. washrinsed with water
  8. customdried in a vacuum oven at 75° C.

Sources & evidence

ORD record
ord-fae50d4856c74ac5b2a59840db523cd5
Source dataset
uspto-grants-2011_03
Patent number
US07897601B2

Reaction notes

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