Реакция #6677

Уравнение реакции

3,5-bis(3′,5′-di-tert-butylstyryl)benzaldehyde

sodium borohydride

→

3,5-bis(3′,5′-di-tert-butylstyryl)benzyl alcohol

Выход 87.0%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Температураwas heated
2. 2
   Температураat reflux for 110 min
3. 3
   ДругоеThe solvent was then completely removed
4. 4
   workup.ADDITIONlight petroleum (30–40) and aqueous hydrochloric acid (3 M, 30 cm3) were added
5. 5
   ФильтрацияThe white precipitate was then filtered
6. 6
   Другоеdried under vacuum

Методика

A mixture of 3,5-bis(3′,5′-di-tert-butylstyryl)benzaldehyde (3.00 g, 6.61 mmol) and sodium borohydride (840 mg, 22.2 mmol) in tetrahydrofuran (150 cm3) was heated at reflux for 110 min. The solvent was then completely removed and light petroleum (30–40) and aqueous hydrochloric acid (3 M, 30 cm3) were added and stirred until effervescence had ceased. The white precipitate was then filtered and dried under vacuum to give 3,5-bis(3′,5′-di-tert-butylstyryl)benzyl alcohol (2.63 g, 87%). A sample for analysis was recrystallised from a dichloromethane-light petroleum (60–80) mixture, mp 226–228° C. (Found: C, 87.28; H, 9.47. C39H52O requires C, 87.26; H, 9.76%); vmax(CHCl3)/cm−1 3608w (OH), 1596 (C═C) and 964 (C═C—H trans); λmax(CH2Cl2)/nm (log ε) 230 (4.42), 307 (4.80), 312 (4.80), 315 (4.80) and 330sh (4.66); δH(500 MHz, CDCl3) 1.41 (36H, s, t-Bu), 1.81 (1H, t, J 6, OH), 4.79 (2H, d, J 6, CH2), 7.16 and 7.27 (4H, d, J 16, 7′, 8′-H), 7.40 (2H, dd, J 1.5, 4′-H), 7.43 (4H, d, J 1.5, 2′, 6′-H), 7.49 (2H, s, 2, 6-H) and 7.66 (1H, s, 4-H); m/z (APCI+) 519 ((M—OH)+, 100%).

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