4-Toluenesulfonyl chloride → (2Z)-3-(2-cyanophenyl)prop-2-enoic acid

HRID 2070832

Reaktionsgleichung

Reaktionsgleichung von HRID 2070832
[N:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[OH:13])=O.C1(C)C=CC(S(Cl)(=O)=[O:21])=CC=1.[OH-].[Na+]>C1COCC1.O>[C:3]([C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1/[CH:6]=[CH:5]\[C:4]([OH:13])=[O:21])#[N:1]

Komponenten

6

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 85801-Nitroso-2-naphtholHCID 14798Sodium Hydroxide

Produkt 1

HCID 1899166(2Z)-3-(2-cyanophenyl)prop-2-enoic acidAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of 1-nitrosonaphthalen-2-ol (5 g) dissolved in THF (30 mL) was treated with p-toluenesulfonyl chloride (6.61 g) under nitrogen. The resulting mixture was stirred at 20° C. for 1 h. The mixture was treated with a solution of sodium hydroxide (4.04 g) in water (30 mL) dropwise over 30 min to keep temperature below 25° C. The reaction mixture was diluted with water (200 mL), and extracted with diethyl ether (200 mL) (discarded). The aqueous layer was acidified with 2M HCl, extracted with ethyl acetate (200 mL), dried (MgSO4), filtered and evaporated. The residue was triturated with 50% diethyl ether in isohexane to give the subtitle compound as a solid (4.75 g).

Aufarbeitung

  1. customtemperature below 25° C
  2. extractionextracted with diethyl ether (200 mL) (discarded)
  3. extractionextracted with ethyl acetate (200 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was triturated with 50% diethyl ether in isohexane

Quellen und Nachweise

ORD-Eintrag
ord-e27be86664be4e5b8c0eeb7d16fe2636
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299246B2

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