Nitric Acid → 1-(4-(Benzyloxy)-5-methoxy-2-nitrophenyl)ethanone

HRID 445466

反応式

HRID 445466 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:20]([O-])([OH:22])=[O:21].S(=O)(=O)(O)O>ClCCl>[CH2:1]([O:8][C:9]1[C:10]([O:18][CH3:19])=[CH:11][C:12]([C:15](=[O:17])[CH3:16])=[C:13]([N+:20]([O-:22])=[O:21])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 944Nitric Acid2 回HCID 1118Sulfuric AcidHCID 992151-(4-Benzyloxy-3-methoxy-phenyl)-ethanone

生成物 1

HCID 534867601-(4-(Benzyloxy)-5-methoxy-2-nitrophenyl)ethanone収率 60%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A stirred solution of 1-(4-benzyloxy-3-methoxyphenyl)ethanone (51.3 g, 200 mmol) in dichloromethane (750 mL) was cooled to 0° C. Nitric acid (90%, 14 mL, 300 mmol) was added dropwise to the cooled solution over 20 min. Sulfuric acid (96.2%, 16.3 mL, 300 mmol) was then added dropwise over 40 min at 0° C. Additional nitric acid (9.4 mL, 200 mmol) was added dropwise over 20 min. The reaction mixture washed with water (3×200 mL), and saturated sodium bicarbonate (4×200 mL, or until neutral). The organic layer was dried over Na2SO4 and concentrated. The crude mixture was recrystallized from DMF to give 1-(4-benzyloxy-5-methoxy-2-nitrophenyl)ethanone (36 g, 60%). 1H NMR (400 MHz, CDCl3): δ 7.65 (s, 1H), 7.45-7.33 (m, 5H), 6.74 (s, 1H), 5.21 (s, 2H), 3.97 (s, 3H), 2.49 (s, 3H).

後処理

  1. washThe reaction mixture washed with water (3×200 mL), and saturated sodium bicarbonate (4×200 mL, or until neutral)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude mixture was recrystallized from DMF

出典と根拠

ORDレコード
ord-14af6f9c6f2a4190b3b3fd2a4e9f343b
出典データセット
uspto-grants-2013_07
特許番号
US08476298B2

関連ノート

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