Dimethylformamide → ethyl 3-methyl-4-nitrobenzoate

HRID 962942ノート

反応式

HRID 962942 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].CN(C)C=O.C(=O)(O)[O-].[Na+].I[CH2:25][CH3:26]>O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([O:7][CH2:25][CH3:26])=[O:6]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 183703-Methyl-4-nitrobenzoic acidHCID 516892Sodium Bicarbonate

生成物 1

HCID 2796918ethyl 3-methyl-4-nitrobenzoate収率 91.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

A mixture of 3-methyl-4-nitrobenzoic acid (1) (362.3 g, 2.0 mol), N,N-dimethylformamide (2000 mL), sodium bicarbonate (200 g, 2.38 mol) and iodoethane (623.9 g, 4.0 mol) was stirred at 70° C. for 18 h. The mixture was allowed to cool to room temperature and poured into water (2000 mL. The resulting solid was collected by filtration, washed with water and dried. The solid was washed further with hexane and dried to provide the title product (382.1 g, 91%) as an off-white solid: mp 51°-52.5° C.; 1H NMR (CDCl3) δ 8.04-7.98 (m, 3H), 4.42 (q, 2H), 2.63 (s, 3H), 1.42 (t, 3H); Mass spectrum (NH3 --CI) m/z 210 (100%, M+H+).

後処理

  1. temperatureto cool to room temperature
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water
  4. customdried
  5. washThe solid was washed further with hexane
  6. customdried

出典と根拠

ORDレコード
ord-767328e277a949d89df8211e8f23f8dd
出典データセット
uspto-grants-1998_06
特許番号
US05760028

反応ノート

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