Hydrochloric Acid → 4-(4-Fluorophenyl)but-3-enoic acid

HRID 1769661Notes

Reaction equation

HRID 1769661 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[Cl-].[C:11]([CH2:14][CH2:15][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:13])=[O:12].CC(C)([O-])C.[K+].[H][H].Cl>O1CCCC1.O.CCOCC>[F:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:15]/[CH2:14][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 680234-FluorobenzaldehydeHCID 10270534(2-Carboxyethyl)triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 178418361HCID 178418361, compound

Product 1

HCID 103973854-(4-Fluorophenyl)but-3-enoic acidYield 50%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

74.4 g of 4-fluorobenzaldehyde and 233.6 g of β-carboxyethyl-triphenyl phosphonium chloride were suspended in 700 ml of tetrahydrofuran and these were incubated on ice and stirred. Into this 500 ml tetrahydrofuran solution of 141.4 g of potassium tert-butoxide was added slowly dropwise. 30 minutes after temperature was brought to room temperature and then they were stirred for 10 hours. After adding thereto ice water and cleaning with ether, the hydrogen-ion concentration of water layer was set to pH2 with undiluted hydrochloric acid. Extraction was then made with ethyl acetate. After drying with magnesium sulfate and concentration made under reduced pressure, the solid obtained was recrystallized from hydrous ethanol, and 53.98 g of marked compound (yield: 50%) was obtained as white needle crystal.

Workup

  1. custom30 minutes
  2. customwas brought to room temperature
  3. stirringthey were stirred for 10 hours
  4. additionAfter adding
  5. extractionExtraction
  6. dry with materialAfter drying with magnesium sulfate and concentration
  7. customthe solid obtained
  8. customwas recrystallized from hydrous ethanol

Sources & evidence

ORD record
ord-5a7dc70e452b4a45974c200674a848b8
Source dataset
uspto-grants-1995_01
Patent number
US05382595

Reaction notes

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