Реакция #50161

Уравнение реакции

4-methoxyphenol

1-bromo-2-methylpentane

→

1-methoxy-4-(2'-methylpentyloxy)benzene

Выход 27.0%

Растворители

methanol

methanol

Условия реакции

Обработка

1. 1
   Температураthis mixture was heated
2. 2
   Температураto reflux for 30 min
3. 3
   ТемператураThe mixture was then heated
4. 4
   Температураto reflux for 16 hours
5. 5
   ДругоеThe solvent was removed in vacuo
6. 6
   workup.DISSOLUTIONthe residue dissolved in ether (200 ml)
7. 7
   Промывкаwashed with dilute aqueous sodium hydroxide (250 ml) and water (500 ml)
8. 8
   Сушкаdried over MgSO4
9. 9
   Концентрированиеconcentrated in vacuo again
10. 10
    workup.DISTILLATIONDistillation at 80° C./0.5 mm Hg

Методика

Sodium metal (6.99 g, 304 mmol) was dissolved in dry methanol (120 ml) under Ar to give a 2.5M solution of sodium methoxide. A solution of 4-methoxyphenol (31.4 g, 253 mmol) in dry methanol (150 ml) was added and this mixture was heated to reflux for 30 min. After cooling to room temperature, a solution of 1-bromo-2-methylpentane (46.0 g, 279 mmol) in dry methanol (100 ml) was added. The mixture was then heated to reflux for 16 hours. The solvent was removed in vacuo, the residue dissolved in ether (200 ml), washed with dilute aqueous sodium hydroxide (250 ml) and water (500 ml), dried over MgSO4 and concentrated in vacuo again. Distillation at 80° C./0.5 mm Hg afforded 14.0g (27%) 1-methoxy-4-(2'-methylpentyloxy)benzene, 1H NMR (250.1 MHz , CDCl3): δ=0.94 (t,3H), 1.02 (d, 3H), 1.16-1.56 (m, 4H), 1.93 (m, 1H), 3.64-3.82 (m, 2H), 3.77 (s, 3H), 6.81-6.89 (m, 4H), 13C NMR (100.6 MHz, CDCl3): δ=14.3, 17.0 (both CH3), 20.1, 35.8 (both CH2), 33.0 (CH), 55.7 (OCH3), 73.9 (OCH2), 114.6, 115.4 (arom. CH), 153.5, 153.6 (ipso C). IR(film): 2956(m), 1509(s), 1232(s), 1045(m), 824 (m) cm-1, MS(EI): m/z (%)=208 (100), 124 (32), Calcd. for C13H20O2 : C 74.96, H 9.68 found: C 75.03, H 9.70.

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