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

HRID 2245190

反応式

HRID 2245190 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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 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 (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 (4 H, 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%).

後処理

  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

出典と根拠

ORDレコード
ord-0f0ccf5ae03e4fed8b088208a6804f63
出典データセット
uspto-grants-2010_03
特許番号
US07682708B2

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