Dichloromethane → 3-(2,2,3,3,3-Pentafluoropropoxy)methyl-4-methyl-1-nitrobenzene

HRID 373361

반응식

HRID 373361 반응식
[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH2:4]Cl.[F:13][C:14]([F:21])([C:17]([F:20])([F:19])[F:18])[CH2:15][OH:16].[OH-].[K+].ClCCl>CN(C)C=O>[F:13][C:14]([F:21])([C:17]([F:20])([F:19])[F:18])[CH2:15][O:16][CH2:4][C:3]1[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:2]=1[CH3:1]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 98722,2,3,3,3-PentafluoropropanolHCID 14797Potassium HydroxideHCID 1879522-(Chloromethyl)-1-methyl-4-nitrobenzene

생성물 1

HCID 150701683-(2,2,3,3,3-Pentafluoropropoxy)methyl-4-methyl-1-nitrobenzene수율 95.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 5.00 g (0.027 mol) of 2-methyl-5-nitrobenzyl chloride and 21.3 g (0.135 mol) of 2,2,3,3,3-pentafluoropropanol in 16.5 ml of dimethylformamide, was added 2.29 g (0.041 mol) of KOH pellets and the solution was stirred overnight. Then dichloromethane was added and the salts were filtered out. The filtrate was made acid and then the solvents were distilled off. The residue was dissolved in a 9/1 (v/v) mixed solvent of hexane/ethyl acetate, washed with dilute hydrochloric acid, water and a saturated sodium chloride aqueous solution, and then dried over magnesium sulfate. The solvents were distilled off and the resulting oil was subjected to silica gel chromatography using hexane/ethyl acetate (19/1, v/v) as developing solvent to obtain 7.71 g of 3-(2,2,3,3,3-pentafluoropropoxy)methyl-4-methyl-1-nitrobenzene having a melting point of 53.5°-54.5° C. in a 95.5% yield.

후처리

  1. filtrationthe salts were filtered out
  2. distillationthe solvents were distilled off
  3. dissolutionThe residue was dissolved in a 9/1 (v/v)
  4. additionmixed solvent of hexane/ethyl acetate
  5. washwashed with dilute hydrochloric acid, water
  6. dry with materiala saturated sodium chloride aqueous solution, and then dried over magnesium sulfate
  7. distillationThe solvents were distilled off

출처 및 근거

ORD 기록
ord-d18683146e0c4b8989faee8f8e73a498
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05162583

연결된 노트

불러오는 중…