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

HRID 1657058

Reaktionsgleichung

Reaktionsgleichung von HRID 1657058
[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]benzonitrile

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
  5. customto 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

Quellen und Nachweise

ORD-Eintrag
ord-8fc204eb0ff4449baeba671ac0fdca04
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05256680

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