HRID411933

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

HCID622077

3,5-Dibromobenzaldehyde

C7H4Br2O

HCID10921928

未命名化合物

HCID66637192

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)c1cc(C=Cc2cc(C=O)cc(C=Cc3cc(C(C)(C)C)cc(C(C)(C)C)c3)c2)cc(C(C)(C)C)c1

HCID54028687

3,5-Bis[2-(3,5-di-tert-butylphenyl)ethenyl]benzaldehyde

C39H50O

收率 139%

AUXILIARIES

试剂、催化剂与溶剂

结构：CC(=O)O.CC(=O)O.[CH2-]c1ccccc1P(c1ccccc1C)c1ccccc1C.[CH2-]c1ccccc1P(c1ccccc1C)c1ccccc1C.[Pd].[Pd]

催化剂HCID11104995

未命名化合物

溶剂HCID31374

Dimethylacetamide

C4H9NO

CONDITIONS

反应条件

温度: 130 °C

PROCEDURE

实验过程

A mixture of 3,5-dibromobenzaldehyde (31.7 g, 120 mmoles), 3,5-di-t-butylstyrene (65.0 g, 301 mmoles), anhydrous sodium carbonate (31.9 g, 301 mmoles), trans-di(μ-acetato)-bis[o-(di-o-tolylphosphino)benzyl]dipalladium (II) (244 mg, 0.26 mmoles, 0.1 mole %), 2,6-di-t-butylcresol (13.3 g, 60 mmoles) and anhydrous N,N-dimethylacetamide (130 mL) was degassed thoroughly whilst stirring under oil-pump vacuum, purging with argon. The reaction mixture was then heated under argon at 130° C. for 26.5 h. After cooling, ether (250 mL) and hydrochloric acid (1.5 M, 150 mL) were added carefully. A suspension remained in the organic layer, which was washed with distilled water (5×125 mL) and evaporated. The combined aqueous layers were extracted with ether (100 mL) and this organic extract was washed with distilled water (4×30 mL) and combined with the main organic fraction. The crude product was triturated thoroughly with cold pet. ether (40-60), filtered and recrystallized from dichloromethane/pet. ether (60-80) to give colourless crystals of 3,5-bis(3′,5′-di-t-butylstyryl)benzaldehyde (44.61 g, 69%), m.p. 217-219° C. (Found: C, 87.7; H, 9.7. C39H50O requires C, 87.6; H, 9.4%); νmax (CHCl3)/cm−1 1698s (C═O), 1596s (C═C) and 964s (C═C—H trans); λmax (CHCl3)/nm 316 (log ε/dm3 mol−1 cm−1 4.65); δH(500 MHz; CDCl3) 1.41 (36H, s, t-Bu), 7.20 and 7.34 (4H, d, J 16, vinyl H), 7.43 (2H, dd, J 2, sp H), 7.44 (4H, d, J 2, sp H), 7.94 (1H, m, cp H), 7.95 (2H, d, J 1.5, cp H) and 10.11 (1H, s, CHO); m/z (APCI+) 535 (M+, 100%).

WORKUP

后处理

customwas degassed thoroughly
custompurging with argon
temperatureAfter cooling
additionether (250 mL) and hydrochloric acid (1.5 M, 150 mL) were added carefully
washwas washed with distilled water (5×125 mL)
customevaporated
extractionThe combined aqueous layers were extracted with ether (100 mL)
extractionthis organic extract
washwas washed with distilled water (4×30 mL)
customThe crude product was triturated thoroughly with cold pet. ether (40-60)
filtrationfiltered
customrecrystallized from dichloromethane/pet. ether (60-80)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-b913bc42de764caf8350632e43ba52ca
来源数据集: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06558818B1
来源说明: uspto-grants-2003_05

反应 SMILES

Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8](Br)[CH:9]=1)[CH:5]=[O:6].[C:11]([C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:22]=1)[CH:18]=[CH2:19])([CH3:14])([CH3:13])[CH3:12].[C:27](=O)([O-])[O-].[Na+].[Na+].[C:33]([C:37]1([CH3:48])[C:42](O)=[C:41]([C:44]([CH3:47])([CH3:46])[CH3:45])[CH:40]=[CH:39][CH2:38]1)([CH3:36])([CH3:35])[CH3:34]>CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd].CN(C)C(=O)C>[C:11]([C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:22]=1)[CH:18]=[CH:19][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH:27]=[CH:38][C:39]2[CH:48]=[C:37]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH:42]=[C:41]([C:44]([CH3:46])([CH3:45])[CH3:47])[CH:40]=2)[CH:9]=1)[CH:5]=[O:6])([CH3:14])([CH3:12])[CH3:13]