p-Toluenesulfonic acid → (E)-1-[3-(4-Chlorophenoxy)phenyl]buten-3-one

HRID 704813

Reaktionsgleichung

Reaktionsgleichung von HRID 704813
[OH-:1].[Na+].[Cl:3][C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH:12]=O)=[CH:6][CH:5]=1.[C:19]1([CH3:29])C=CC(S(O)(=O)=O)=C[CH:20]=1>CC(C)=O.C1(C)C=CC=CC=1>[Cl:3][C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]2[CH:10]=[C:11](/[CH:12]=[CH:20]/[C:19](=[O:1])[CH3:29])[CH:14]=[CH:15][CH:16]=2)=[CH:6][CH:5]=1

Komponenten

6

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 6160153-(4-Chlorophenoxy)benzaldehyde

Produkt 1

HCID 20073366(E)-1-[3-(4-Chlorophenoxy)phenyl]buten-3-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

10 N aqu. NaOH (2 ml) was added to a solution of 3-(4-chlorophenoxy)-benzaldehyde (23.3 g, Aldrich) in acetone (150 ml) and stirred vigorously. After a few minutes' stirring, the temperature rose to 32° C. The mixture was left for 5 minutes and then poured into 2 M aqu. HCl (600 ml) and extracted with ether/pet. ether (1:1, 200 ml). The extract was washed with water and satd. aqu. NaCl, dried over MgSO4, and stripped to give the aldol product. The latter was taken up in toluene (300 ml), p-toluenesulphonic acid (1 g) was added, and the mixture heated for 1 hour. The mixture was then cooled, washed with satd. aqu. NaHCO3 and satd. aqu. NaCl, dried over MgSO4 and stripped. The residue was eluted through a slice gel column using methylene chloride/40-60 pet. ether (1:1, followed by 3:1) and the eluate stripped to give the desired product (19 g).

Aufarbeitung

  1. stirringAfter a few minutes' stirring
  2. customrose to 32° C
  3. additionpoured into 2 M aqu
  4. extractionHCl (600 ml) and extracted with ether/pet. ether (1:1, 200 ml)
  5. washThe extract was washed with water and satd
  6. dry with materialNaCl, dried over MgSO4
  7. customto give the aldol product
  8. temperaturethe mixture heated for 1 hour
  9. temperatureThe mixture was then cooled
  10. washwashed with satd
  11. dry with materialNaCl, dried over MgSO4
  12. washThe residue was eluted through a slice gel column

Quellen und Nachweise

ORD-Eintrag
ord-b20afd6f017c485282cb258baae5a590
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04988733

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