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

HRID 1178175

Reaction equation

HRID 1178175 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%); νmax(CHCl3)/cm−1 3608 w (OH), 1596 (C═C) and 964 (C═C—H trans); λmax(CH2Cl2)/nm (logε) 230 (4.42), 307 (4.80), 312 (4.80), 315 (4.80) and 330 sh (4.66); δH(500 MHz, CDCl3) 1.41 (36 H, s, t-Bu), 1.81 (1 H, t, J 6, OH), 4.79 (2 H, d, J 6, CH2), 7.16 and 7.27 (4H, d, J 16, 7′,8′-H), 7.40 (2 H, dd, J 1.5, 4′-H), 7.43(4 H, d, J 1.5, 2′,6′-H), 7.49 (2 H, s, 2,6-H) and 7.66 (1 H, 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-a9a087b2a86c40379418e7d8fbb0fc36
Source dataset
uspto-grants-2007_10
Patent number
US07276299B2

Linked notes

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