1-Bromopentane → 2-n-Pentoxy-5-nonyl benzophenone

HRID 483071

Reaktionsgleichung

Reaktionsgleichung von HRID 483071
[OH:1][C:2]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[OH-].[Na+].[CH2:27](Br)[CH2:28][CH2:29][CH2:30][CH3:31]>C(Cl)Cl.O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:27]([O:1][C:2]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5])[CH2:28][CH2:29][CH2:30][CH3:31]

Komponenten

7

Edukt 3

HCID 80571-BromopentaneHCID 14798Sodium HydroxideHCID 93939Methanone, (2-hydroxy-5-nonylphenyl)phenyl-

Produkt 1

HCID 538938732-n-Pentoxy-5-nonyl benzophenoneAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 2-hydroxy-5-nonyl benzophenone, 15 g, in 100 mL methylene chloride was mixed with a solution of 9.25 g NaOH in 100 mL water. To this mixture was added 6.9 g n-pentyl bromide and 1.48 g tetra-n-butylammonium bromide. The whole mixture was then vigorously agitated overnight at 40° C. After cooling to room temperature with 50 mL CH2Cl2. The combined methylene chloride layers were concentrated to an oil, which was taken up in 100 mL petroleum ether and washed with 100 mL water. Finally, the organic layer was dried over anhydrous magnesium sulfate and the volatiles removed under vacuum to give 15 g (82% yield) of 2-n-pentoxy-5-nonyl benzophenone.

Aufarbeitung

  1. customvigorously agitated overnight
  2. customat 40° C
  3. concentrationThe combined methylene chloride layers were concentrated to an oil, which
  4. washwashed with 100 mL water
  5. dry with materialFinally, the organic layer was dried over anhydrous magnesium sulfate
  6. customthe volatiles removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c311d96f2e954f6182650344fbe57b25
Quelldatensatz
uspto-grants-1986_03
Patentnummer
US04578250

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