Reaktion #2460289

Reaktionsgleichung

2,4-di-(tert-amyl)phenol

methyl 2-bromobenzoate

→

methyl 2,4-di-(tert-amyl)phenoxybenzoate

Lösungsmittel

pyridine

pyridine

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenTo a stirred suspension under argon of sodium hydride (60% dispersion in mineral oil, 1.1 g, 46.5 mmol, washed with ligroin
2. 2
   Sonstigeto remove the oil) in pyridine (60 mL)
3. 3
   Temperaturthe mixture was heated
4. 4
   Temperaturat reflux 16 h
5. 5
   Temperaturcooled
6. 6
   Waschenwashed successively with 10% aqueous HCl, water, and brine
7. 7
   Trocknendried over Na2SO4
8. 8
   SonstigeThe solvent was removed at reduced pressure
9. 9
   SonstigeThis crude product was purified by column chromatography
10. 10
    Sonstigeto give 25.5 g, 78% of theory) of a light brown oil

Vorschrift

First, methyl 2,4-di-(tert-amyl)phenoxybenzoate was prepared. To a stirred suspension under argon of sodium hydride (60% dispersion in mineral oil, 1.1 g, 46.5 mmol, washed with ligroin to remove the oil) in pyridine (60 mL) was added dropwise a solution of 2,4-di-(tert-amyl)phenol (12.0 g, 51.2 mmol) in 20 mL of pyridine. The mixture was stirred for 2 h at room temperature and then treated dropwise with a solution of methyl 2-bromobenzoate (10 g, 46.5 mmol) in 10 mL of pyridine. Copper (I) chloride (1.15 g, 11.6 mmol) was added, and the mixture was heated at reflux 16 h and then cooled to ambient. The mixture was diluted with diethyl ether, washed successively with 10% aqueous HCl, water, and brine, and then dried over Na2SO4. The solvent was removed at reduced pressure to deposit dark brown oil. This crude product was purified by column chromatography to give 25.5 g, 78% of theory) of a light brown oil. 1H NMR (CDCl3): δ 0.70 (t, 6H), 1.3 (s, 6H), 1.4 (s, 6H), 1.63 (q, 2H), 1.85 (q, 2H), 3.85 (s, 3H), 6.68 (d, 1H), 6.82 (d, 1H), 7.05 (m, 2H), 7.3 (br s, 1H), 7.35 (t, 1H), 7.9 (dd, 1H).

Quelle