Sodium borohydride → 3,5-Bis(3',5'-di-tert-butylstyryl)benzyl alcohol
Reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:34]=[C:35]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH:36]=1)[CH:8]=[CH:9][C:10]1[CH:11]=[C:12]([CH:15]=[C:16]([CH:18]=[CH:19][C:20]2[CH:25]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:23]=[C:22]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:21]=2)[CH:17]=1)[CH:13]=[O:14])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>O1CCCC1>[C:1]([C:5]1[CH:6]=[C:7]([CH:34]=[C:35]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH:36]=1)[CH:8]=[CH:9][C:10]1[CH:11]=[C:12]([CH:15]=[C:16]([CH:18]=[CH:19][C:20]2[CH:21]=[C:22]([C:30]([CH3:31])([CH3:32])[CH3:33])[CH:23]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:25]=2)[CH:17]=1)[CH2:13][OH:14])([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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%).