Sodium borohydride → 3,5-Bis(3',5'-di-tert-butylstyryl)benzyl alcohol

HRID 6581

Reaction equation

HRID 6581 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

HCID 4311764Sodium borohydrideHCID 540286873,5-Bis[2-(3,5-di-tert-butylphenyl)ethenyl]benzaldehyde

Product 1

HCID 674021763,5-Bis(3',5'-di-tert-butylstyryl)benzyl alcoholYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 110 min
  3. customThe solvent was then completely removed
  4. additionlight petroleum (30–40) and aqueous hydrochloric acid (3 M, 30 cm3) were added
  5. filtrationThe white precipitate was then filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-ba5e0dbceb244edeabb972ef6039049c
Source dataset
uspto-grants-2006_08
Patent number
US07083862B2

Linked notes

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