Acetic Anhydride → 2-(Acetyloxy)-4-methylbenzonitrile

HRID 1157859

Reaktionsgleichung

Reaktionsgleichung von HRID 1157859
[OH:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:11](OC(=O)C)(=[O:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[C:11]([O:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])(=[O:13])[CH3:12]

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 143886562-Hydroxy-4-methylbenzonitrile

Produkt 1

HCID 450912002-(Acetyloxy)-4-methylbenzonitrileAusbeute 97,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2-Hydroxy-4-methylbenzonitrile (0.563 g, 4.23 mmol) in CH2Cl2 (21 mL) was added acetic anhydride (0.60 mL, 6.36 mmol) followed by triethylamine (1.20 mL, 8.61 mmol) and the resultant solution was stirred at room temperature for 30 minutes. The mixture was diluted with CH2Cl2 (60 mL), washed with saturated aqueous NaHCO3 (20 mL) and brine (2×20 mL). The organic phase was dried (Na2SO4) and concentrated and provided 0.72 g (97%) of (2-cyano-5-methyl-phenyl) acetate as a white solid. 1H NMR (CDCl3) δ 2.38 (s, 3H), 2.43 (s, 3H), 7.08 (s, 1H), 7.13 (d, 1H, J=9 Hz), 7.54 (d, 1H, J=9 Hz).

Aufarbeitung

  1. washwashed with saturated aqueous NaHCO3 (20 mL) and brine (2×20 mL)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e4fd0ccdac754e1a8baa3ce7b9705d4c
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807694B2

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