Hydrochloric Acid → 3,4-Bis(4-methoxyphenyl)hex-3-ene

HRID 28274

Reaktionsgleichung

Reaktionsgleichung von HRID 28274
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][CH3:11])=[CH:5][CH:4]=1.Cl>O1CCCC1>[CH3:6][CH2:9]/[C:10](/[C:11]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)=[C:9](\[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)/[CH2:11][CH3:10]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 671444-Propanoylanisole

Produkt 1

HCID 30325393,4-Bis(4-methoxyphenyl)hex-3-eneAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Zinc dust (654 mg, 10.0 mmol) was slurried in 20 ml dry tetrahydrofuran under an inert atmosphere, and a solution of titanium tetrachloride (0.55 ml, 5.0 mmol) in 3 ml dry benzene was added. The resulting mixture was refluxed overnight to form active Ti(II) reagent, and a solution of para-methoxypropiophenone (500 mg, 3.0 mmol) in 5 ml dry tetrahydrofuran was added. After refluxing for twelve hours, the solution was cooled to room temperature, poured into 50 ml 2 N aqueous hydrochloric acid, and extracted with ether. The ether extracts were combined, washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated by solvent removal at the rotary evaporator. The residue was purified by chromatography on silica gel to give 410 mg (91%) dimestrol identified by ir, nmr, and mass spectra; mp 124°.

Aufarbeitung

  1. temperatureAfter refluxing for twelve hours
  2. extractionextracted with ether
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated by solvent removal at the rotary evaporator
  6. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-5685acae4bf74a8e996b55dda6621556
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04225734

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