1-(Chloromethoxy)-2-methoxyethane → 3,5-Bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy)methoxy]benzonitrile

HRID 466040

Reaktionsgleichung

Reaktionsgleichung von HRID 466040
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6]Cl.[CH3:8][C:9]([C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]=1[OH:20])[C:15]#[N:16])([CH3:11])[CH3:10].C(N(C)C(C)C)(C)C>C(Cl)Cl>[CH3:24][C:21]([C:18]1[CH:17]=[C:14]([CH:13]=[C:12]([C:9]([CH3:11])([CH3:10])[CH3:8])[C:19]=1[O:20][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[C:15]#[N:16])([CH3:22])[CH3:23]

Komponenten

5

Edukt 3

HCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 137274Benzonitrile, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-HCID 547370N,N-Diisopropylmethylamine

Produkt 1

HCID 100416433,5-Bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy)methoxy]benzonitrileAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2-Methoxyethoxymethyl chloride (4.1 g, 0.032 mole) is added dropwise to a 0° C. mixture of 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzonitrile (Louis A. Cohen, Journal of Organic Chemistry 22, 1333, 1957) (5.0 g, 0.022 mole) and diisopropylaminomethane (4.2 g, 0.032 mole) in methylene chloride (50 ml). The mixture is allowed to warm to room temperature and stir 18 hours. The solution is diluted with methylene chloride (25 ml) and washed with water (25 ml), cold 2M HCl (20 ml), saturated aqueous NaCl, and dried over MgSO4. Filtered and concentrated in vacuo to obtain 6.7 g (6.9 g theor., 97%) of 3,5-bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy)methoxy]benzonitrile as a yellow oil.

Aufarbeitung

  1. washwashed with water (25 ml), cold 2M HCl (20 ml), saturated aqueous NaCl
  2. dry with materialdried over MgSO4
  3. filtrationFiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-edcad62bf0124dd18582110a8b7b330a
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05155122

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