Water → 1-Bromo-5-tert-butyl-4-(2-methoxy-ethoxymethoxy)-2-methyl-benzene

HRID 356495

Reaktionsgleichung

Reaktionsgleichung von HRID 356495
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:3]=1.[H-].[Na+].[CH3:16][O:17][CH2:18][CH2:19][O:20][CH2:21]Cl.O>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:10]([CH3:13])([CH3:12])[CH3:11])[C:5]([O:9][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:6][C:7]=1[CH3:8]

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 187986984-Bromo-2-(tert-butyl)-5-methylphenol

Produkt 1

HCID 187986651-Bromo-5-tert-butyl-4-(2-methoxy-ethoxymethoxy)-2-methyl-benzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 4-bromo-2-t-butyl-5-methylphenol from Example YY (32.8 g, 135 mmol) in THF (150 mL) was treated portionwise with NaH (6.5 g of a 60% dispersion in oil, 162 mmol), and the mixture was stirred at room temperature for 1 hour. To the suspension was added 2-methoxyethoxymethyl chloride (18 mL, 158 mmol) all at once, and the resulting mixture was stirred at room temperature overnight. H2O (200 mL) was added slowly, followed by EtOAc (200 mL). The organic layer was separated, washed with H2O, and dried (MgSO4). Concentration gave the title compound. 1H NMR (CDCl3) δ 1.31 (s, 9 H), 2.29 (s, 3 H), 3.36 (s, 3 H), 3.55 (m, 2 H), 3.78 (m, 2 H), 5.25 (s, 2 H), 7.02 (s, 1 H), 7.33 (s, 1 H).

Aufarbeitung

  1. stirringwas stirred at room temperature overnight
  2. customThe organic layer was separated
  3. washwashed with H2O
  4. dry with materialdried (MgSO4)
  5. concentrationConcentration

Quellen und Nachweise

ORD-Eintrag
ord-13f8efb0331a46d6b54d8a70e8fc9d07
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05834506

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