Acetic Acid → 12-(3,5-Di-tert-butyl-4-hydroxyphenylthio)dodecanoic acid

HRID 1090999

Reaktionsgleichung

Reaktionsgleichung von HRID 1090999
[C:1]([C:5]1[CH:10]=[C:9]([SH:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30].[OH-].[Na+].C(O)(=O)C>C(O)C.O>[C:1]([C:5]1[CH:10]=[C:9]([S:11][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 17546812-Bromododecanoic Acid

Produkt 1

HCID 1479623112-(3,5-Di-tert-butyl-4-hydroxyphenylthio)dodecanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 2,6-di-tert-butyl-4-mercaptophenol (II) (477 mg; 2 mmol) in dry ethanol (20 ml), water containing 12-bromododecanoic acid (558 mg; 2 mmol) and 97 % sodium hydroxide (250 mg; 6 mmol) was added, and the resultant mixture was allowed to stand at room temperature for 20 hours. The reaction mixture was made acidic with 10 aqueous acetic acid and extracted with ethyl acetate. The extract was washed two times with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product thus obtained was chromatographed on silica gel and eluted with ethyl acetate. The collected fractions were concentrated under reduced pressure. The residue was recrystallized from a mixture of water and methanol (1 : 1 by volume) to give the objective compound (Ie) (680 mg). Yield, 78 %. m.p., 41°-42° C.

Aufarbeitung

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed two times with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1cad54b8c8e74ef6b54cbcb8bd641d67
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05084214

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