반응 #2460289

반응 방정식

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

methyl 2-bromobenzoate

→

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

용매

pyridine

pyridine

diethyl ether

반응 조건

후처리

1. 1
   세척To a stirred suspension under argon of sodium hydride (60% dispersion in mineral oil, 1.1 g, 46.5 mmol, washed with ligroin
2. 2
   기타to remove the oil) in pyridine (60 mL)
3. 3
   온도the mixture was heated
4. 4
   온도at reflux 16 h
5. 5
   온도cooled
6. 6
   세척washed successively with 10% aqueous HCl, water, and brine
7. 7
   건조dried over Na2SO4
8. 8
   기타The solvent was removed at reduced pressure
9. 9
   기타This crude product was purified by column chromatography
10. 10
    기타to give 25.5 g, 78% of theory) of a light brown oil

실험 절차

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).

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