Ethylene Glycol → 3,3-Diphenylacrylic acid

HRID 469263

Reaktionsgleichung

Reaktionsgleichung von HRID 469263
[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=CC#N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:17].[Na+].Cl.[CH2:20]([OH:23])[CH2:21]O>O>[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:21][C:20]([OH:23])=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2743523,3-Diphenylacrylonitrile

Produkt 1

HCID 118263,3-Diphenylacrylic acidAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A mixture of 3,3-diphenylacrylonitrile (5.76 g, 28.1 mmol) and sodium hydroxide (11.2 g) in ethylene glycol (180 mL) and water (1 mL) were refluxed for 3 days. The reaction mixture was diluted with water (100 mL), acidified with 5N HCl to pH˜1, and extracted with ethyl acetate. The organic extract was washed with water, dried over sodium sulfate, and concentrated in vacuo. The crude material was purified by flash column chromatography ethyl acetate/hexanes to give 3,3-diphenylacrylic acid (5.1 g, 81%) as a white powder.

Aufarbeitung

  1. temperaturewere refluxed for 3 days
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash column chromatography ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-4013f70533ea4b51b777c2b2ef3ec886
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629149B2

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