Bisphenol A → HCID 71257395, Verbindung

HRID 705317

Reaktionsgleichung

Reaktionsgleichung von HRID 705317
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)([CH3:12])[CH3:11])=[CH:6][CH:5]=1.Cl[CH2:21][C@H:22]1[CH2:26][O:25][C:24]([CH3:28])([CH3:27])[O:23]1>CN(C)C=O>[CH3:27][C:24]1([CH3:28])[O:23][C@@H:22]([CH2:21][O:3][C:4]2[CH:5]=[CH:6][C:7]([C:10]([C:13]3[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=3)([CH3:12])[CH3:11])=[CH:8][CH:9]=2)[CH2:26][O:25]1

Komponenten

5

Edukt 3

HCID 6623Bisphenol AHCID 24758Sodium hydrideHCID 2734443(R)-(+)-4-(Chloromethyl)-2,2-dimethyl-1,3-dioxolane

Produkt 1

HCID 71257395HCID 71257395, VerbindungAusbeute 23,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (60% dispersion in mineral oil, 1750 mg, 43.80 mmol, 1.0 equiv) was added slowly to a stirred solution of Bisphenol A (10000 mg, 43.80 mmol, 1 equiv) in anhydrous dimethyl formamide (30 mL), at room temperature, and the contents were stirred under an atmosphere of argon for 20 min. (R)-(+)-4-chloromethyl-2,2-dimethyl-1,3-dioxolane 98% (7.10 mL, 52.56 mmol, 1.2 equiv) was added via syringe and the mixture was allowed to react at 70-80° C. for 40 h. Then, the reaction was quenched by the addition of a saturated solution of ammonium chloride (10 mL), and the mixture was extracted with ethyl acetate (3×20 mL). The organic layer was washed with deionized water (25 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel (eluent: 10% ethyl acetate in hexane) to provide the title compound (3560 mg, 24%, 25-30% conversion) as a foam.

Aufarbeitung

  1. additionwas added via syringe
  2. customto react at 70-80° C. for 40 h
  3. customThen, the reaction was quenched by the addition of a saturated solution of ammonium chloride (10 mL)
  4. extractionthe mixture was extracted with ethyl acetate (3×20 mL)
  5. washThe organic layer was washed with deionized water (25 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by flash column chromatography on silica gel (eluent: 10% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-5bb38725d5aa4f0d868f2a52c4e30619
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09173939B2

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