Nitric Acid → Butanoic acid, 4-(4-formyl-2-methoxy-5-nitrophenoxy)-, methyl ester

HRID 476395

反応式

[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[O:15])=[CH:10][C:9]=1[O:16][CH3:17].[N+:19]([O-])([OH:21])=[O:20].O>C(OC(=O)C)(=O)C>[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[C:12]([N+:19]([O-:21])=[O:20])[C:11]([CH:14]=[O:15])=[CH:10][C:9]=1[O:16][CH3:17]

参加物

反応条件

温度: 0 °C

実験手順

A solution of the aldehyde 11 (50 g, 0.197 mol) in acetic anhydride (150 mL) was slowly added to a mixture of 70% nitric acid (900 mL) and acetic anhydride (200 mL) at 0° C. and was then left to stir for 2.5 hours at 0° C. The solution was then poured onto ice in a 5 L flask and the volume adjusted to 5 L with ice and water. The resulting light sensitive pale yellow precipitate was immediately filtered (the ester is slowly hydrolysed at room temperature in those conditions) and washed with cold water. The product 12 was used directly in the next step. TLC analysis (50/50 EtOAc/Pet Et) proved the product pure. 1H NMR (CDCl3) δ 10.4 (2H, s), 7.61 (1H, s), 7.4 (1H, s), 4.21 (2H, t, J=6.2 Hz), 4.00 (3H, s), 3.71 (2H, s), 2.58 (2H, t, J=7.1 Hz), 2.23 (2H, p, J=6.3 Hz); 13C NMR (CDCl3) δ 188.5, 172.8, 152.7, 151.0, 143.5, 124.7, 110.1, 108.2, 68.4, 56.4, 51.3, 29.7, 23.8; MS (ES+) m/z (relative intensity) 298 ([M+H]+, 100).

後処理

waitwas then left
additionThe solution was then poured onto ice in a 5 L flask
filtrationThe resulting light sensitive pale yellow precipitate was immediately filtered (the ester
customis slowly hydrolysed at room temperature in those conditions
washwashed with cold water

出典と根拠

ORDレコード: ord-9a522050909847d0a0beecbf4fd7a83b
出典データセット: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08637664B2

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

関連ノート