Acetic Acid → Ethyl 3-(4-cyano-3-hydroxyphenyl)propanoate

HRID 1937780Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1937780
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][C:4]=1[O:16]C)#[N:2].[C-]#N.[Na+].CC(O)=O>CS(C)=O.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][C:4]=1[OH:16])#[N:2]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 22461741Ethyl 3-(4-cyano-3-methoxyphenyl)propionate

Produkt 1

HCID 9834402Ethyl 3-(4-cyano-3-hydroxyphenyl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of ethyl 3-(4-cyano-3-methoxyphenyl)propionate (3.17 g, 13.6 mmol, 1 equiv) and sodium cyanide (2.00 g, 40.8 mmol, 3.00 equiv) in DMSO (60 mL) was stirred at 140-180° C. for 2 h. After 2.5 hours the reaction mixture was taken up in H2O (300 mL), adjusted to pH 7 with AcOH (2.1 mL), and extracted with Et2O (1×150 mL). The organic layer was washed with H2O (2×50 mL), dried (anh. Na2SO4), and concentrated (75° C.). This yielded 2.05 g (68.8%) of ethyl 4-(4-cyano-3-hydroxyphenyl)propionate as a light yellow crystalline solid: 1H-NMR (CDCl3) 7.42 (1H, d), 7.40 (1H, br s), 6.92 (1H, d), 6.81 (1H, dd), 4.15 (2H, q), 2.94 (2H, dd), 2.64 (2H, dd), 1.25 (3H, t).

Aufarbeitung

  1. extractionextracted with Et2O (1×150 mL)
  2. washThe organic layer was washed with H2O (2×50 mL)
  3. dry with materialdried (anh. Na2SO4)
  4. concentrationconcentrated (75° C.)

Quellen und Nachweise

ORD-Eintrag
ord-0be0cba3c0134771b61f78e1ebfd5c3f
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06395919B1

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