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

HRID 33987

反応式

HRID 33987 の反応式
[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

5

反応物 3

HCID 944Nitric AcidHCID 962WaterHCID 10753291Methyl 4-(4-formyl-2-methoxyphenoxy)butanoate

生成物 1

HCID 11033807Butanoic acid, 4-(4-formyl-2-methoxy-5-nitrophenoxy)-, methyl ester収率 62%

試薬・触媒・溶媒 1

HCID 7918Acetic Anhydride溶媒2 回

実験手順

A solution of the keto-ester (48)(20.00 g, 79.3 mmol) in acetic anhydride (80 mL) was added dropwise to a stirring solution of HNO3 (400 mL) and Ac2O (80 mL) at 0° C. After stirring for 2.5 hours the reaction mixture was poured into iced water (3 L) and allowed to stand at 4° C. for a further 16 hours. The precipitate was collected by filtration and dried under vacuum to provide the nitro compound (49) as a yellow crystalline solid (14.52 g, 62%). Melting Point 70-73° C. 1H NMR (250 MHz, CDCl3) δ 10.4 (s, 2H), 7.61 (s, 1H), 7.40 (s, 1H), 4.21 (t, J=6.2 Hz, 2H), 4.00 (s, 3H), 3.71 (s, 3H), 2.58 (t, J=7.1 Hz, 2H), 2.23 (pent, J=6.3 Hz, 2H). 13C NMR (67.8 MHz, CDCl3) 188.2 (C1), 173.7 (C12), 153.8 (Cquat.), 152.1 (Cquat.), 144.1 (Cquat.), 125.8 (Cquat.), 110.2 (C6), 108.5 (C3), 69.0 (C9), 57.0 (C8), 52.2 (C13), 30.6 (C11), 24.4 (C10). IR (cm−1) 3571, 3485, 2951, 1725, 1689, 1573, 1329, 1172, 1064, 1002, 936, 896, 858, 820, 766, 738, 688, 624. MS (M+1) 298.0. Anal. Calcd for C13H15NO7: C, 52.53; H, 5.09; N, 4.71. Found: C, 52.80; H, 5.03; N, 4.75.

後処理

  1. waitto stand at 4° C. for a further 16 hours
  2. filtrationThe precipitate was collected by filtration
  3. customdried under vacuum

出典と根拠

ORDレコード
ord-d15a5165251245e5adaa94945b28ea16
出典データセット
uspto-grants-2008_09
特許番号
US07429658B2

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