4-Methoxyphenol → Methyl 3,5-dinitro-4-(4-methoxyphenoxy)-benzoate

HRID 564838

반응식

HRID 564838 반응식
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.Cl[C:13]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=1[N+:26]([O-:28])=[O:27]>O>[N+:26]([C:14]1[CH:15]=[C:16]([CH:21]=[C:22]([N+:23]([O-:25])=[O:24])[C:13]=1[O:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH3:3])=[CH:6][CH:7]=1)[C:17]([O:19][CH3:20])=[O:18])([O-:28])=[O:27]

참가 물질

5

반응물 3

HCID 90154-MethoxyphenolHCID 14797Potassium HydroxideHCID 96161Methyl 4-chloro-3,5-dinitrobenzoate

생성물 1

HCID 9819693Methyl 3,5-dinitro-4-(4-methoxyphenoxy)-benzoate수율 65.6%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
150 °C

실험 절차

To a 100 ml round-bottomed flask containing potassium hydroxide (4.7 g; 82.0 mmol) dissolved in water (20 ml) was successively added 4-methoxyphenol (10.0 g; 80.6 mmol) and methyl 4-chloro-3,5-dinitrobenzoate (20.2 g; 77.5 mmol). The flask was fitted with a reflux condenser and the reaction heated at 150° C. (oil bath) for 3 hours. After cooling to room temp, the reaction mixture was transferred to a large mortar and triturated with cold 2N NaOH (100 ml) to remove unreacted phenol. The solid was collected by filtration and air-dried to give 21.5 g of crude product. Crystallization from absolute ethanol gave 17.7 g (65.6%) of pure methyl 3,5-dinitro-4-(4-methoxyphenoxy)benzoate as light yellow needles. 300 MHz 1H NMR (CDCl3) d 3.77 (s, 3H, OCH3), 4.02 (s, 3H, OCH3), 6.82 (m, 4H, ArH), 8.70 (s, 2H, ArH).

후처리

  1. customThe flask was fitted with a reflux condenser
  2. temperatureAfter cooling to room temp
  3. customtriturated with cold 2N NaOH (100 ml)
  4. customto remove unreacted phenol
  5. filtrationThe solid was collected by filtration
  6. customair-dried
  7. customto give 21.5 g of crude product
  8. customCrystallization from absolute ethanol

출처 및 근거

ORD 기록
ord-dbd37e4eeec946bb917c348fb12ef5ff
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06169104A

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