تفاعل #2460289

معادلة التفاعل

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

methyl 2-bromobenzoate

→

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

المذيبات

pyridine

pyridine

diethyl ether

ظروف التفاعل

المعالجة

1. 1
   غسيلTo a stirred suspension under argon of sodium hydride (60% dispersion in mineral oil, 1.1 g, 46.5 mmol, washed with ligroin
2. 2
   أخرىto remove the oil) in pyridine (60 mL)
3. 3
   درجة الحرارةthe mixture was heated
4. 4
   درجة الحرارةat reflux 16 h
5. 5
   درجة الحرارةcooled
6. 6
   غسيلwashed successively with 10% aqueous HCl, water, and brine
7. 7
   تجفيفdried over Na2SO4
8. 8
   أخرىThe solvent was removed at reduced pressure
9. 9
   أخرىThis crude product was purified by column chromatography
10. 10
    أخرىto give 25.5 g, 78% of theory) of a light brown oil

الإجراء التجريبي

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).

المصدر