Dimethylformamide → ethyl 3-methyl-4-nitrobenzoate

HRID 962942노트

반응식

HRID 962942 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 2796918ethyl 3-methyl-4-nitrobenzoate수율 91.3%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-767328e277a949d89df8211e8f23f8dd
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05760028

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