Water → 8-Phenyl-3,5,7-octatrienoic acid

HRID 2299598Notes

Reaction equation

HRID 2299598 reaction equation
[C:1]1([CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[OH2:15].[O:16]1[CH2:20][CH2:19][CH2:18]C1>CS(C)=O>[C:1]1([CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=[CH:18][CH2:19][C:20]([OH:16])=[O:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 1146512,4-Pentadienal, 5-phenyl-

Product 1

HCID 850637148-Phenyl-3,5,7-octatrienoic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 5-phenyl-2,4-pentadienal (15 g) and 3-(triphenylphosphonium)-propionic acid chloride (35.2 g) in 140 mL each of anhydrous tetrahydrofuran and anhydrous dimethyl sulfoxide was added dropwise to sodium hydride (4.6 g) at 0-5° C. under nitrogen over a period of four hours. The reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was cooled to 0-5° C. and water (280 mL) was added dropwise over a period of 30 minutes. The aqueous layer was extracted with ethyl acetate (280 mL) twice, acidified with 12 N hydrochloric acid (24 mL) to a pH of 1, extracted again with ethyl acetate (280 mL) twice. The combined organic layers were washed with water (500 mL) twice, dried over anhydrous sodium sulfate and concentrated under vacuum to give an oil. The oily crude product was chromatographed on a Biotage 40M silica gel column and eluted with methylene chloride:ethyl acetate (95:5). The fractions containing the desired product were combined and the solvents were removed under vacuum to afford 0.7 g of 8-phenyl-3,5,7-octatrienoic acid. 1H NMR (acetone-d6, 300 MHz), δ(ppm) 7.46 (m, 2H), 7.26 (m, 3H), 6.95 (m, 1H), 6.60 (d, 1H), 6.34 (m, 3H), 5.87 (m, 1H), 3.17 (d, 2H).

Workup

  1. temperatureThe reaction mixture was cooled to 0-5° C.
  2. extractionThe aqueous layer was extracted with ethyl acetate (280 mL) twice
  3. extractionextracted again with ethyl acetate (280 mL) twice
  4. washThe combined organic layers were washed with water (500 mL) twice
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customto give an oil
  8. customThe oily crude product was chromatographed on a Biotage 40M silica gel column
  9. washeluted with methylene chloride:ethyl acetate (95:5)
  10. additionThe fractions containing the desired product
  11. customthe solvents were removed under vacuum

Sources & evidence

ORD record
ord-01d3012ee19445d0bab54b7ffb915d57
Source dataset
uspto-grants-2002_12
Patent number
US06495719B2

Reaction notes

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