Sodium Hydroxide → 2,6-Di-sec-butylphenol

HRID 540742

Reaktionsgleichung

Reaktionsgleichung von HRID 540742
[CH:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH2:13][CH3:14])[CH3:12])[C:6]=1[O:15]C(=O)N)([CH2:3][CH3:4])[CH3:2].[OH-].[Na+]>O1CCOCC1>[CH:11]([C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([CH:1]([CH2:3][CH3:4])[CH3:2])[C:6]=1[OH:15])([CH2:13][CH3:14])[CH3:12]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 66725334Carbamic acid 2,6-di-sec-butylphenyl ester

Produkt 1

HCID 216852,6-Di-sec-butylphenolAusbeute 100,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

R-(+)-1-Phenyl-ethyl)-carbamic acid (−) 2,6-di-sec-butylphenyl ester (1b) (4.1 g, 11.6 mmol) was dissolved in a 100 ml 1:1 mixture of dioxane: 1M NaOH aq. The reaction mixture was stirred at 70° C. for 15 min. Volatiles were removed at reduced pressure to a volume of ˜50-70 ml. The pH was adjusted to 3-4 with 1M HCl. The phenol was extracted with ether (3×50 ml), washed with 1 M HCl, brine and dried over anhydrous MgSO4. Evaporation yielded crude yellow oil (2.4 g, ˜100%). Vacuum distillation was performed (120-125° C./˜5 mm) (2.1 g, 89%). Optical rotation: α20D=−14.11° (c=2, pentane).

Aufarbeitung

  1. customVolatiles were removed at reduced pressure to a volume of ˜50-70 ml
  2. extractionThe phenol was extracted with ether (3×50 ml)
  3. washwashed with 1 M HCl, brine
  4. dry with materialdried over anhydrous MgSO4
  5. customEvaporation

Quellen und Nachweise

ORD-Eintrag
ord-adf940e11111468e8d881097bac8f4c3
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871815B2

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