Sulfuric Acid → 6-Chlorohexyl 2-(4-nitrobenzyl)-3-(4-nitrophenyl)propanoate

HRID 1671536노트

반응식

HRID 1671536 반응식
[N+:1]([C:4]1[CH:27]=[CH:26][C:7]([CH2:8][C:9]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)([C:13]([OH:15])=[O:14])C(O)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]O.S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:27]=[CH:26][C:7]([CH2:8][CH:9]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=2)[C:13]([O:15][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][Cl:28])=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 748286-Chloro-1-hexanolHCID 229285922,2-Bis(4-nitrobenzyl)malonic acid

생성물 1

HCID 593812656-Chlorohexyl 2-(4-nitrobenzyl)-3-(4-nitrophenyl)propanoate수율 78.4%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

1.00 g (2.67 mmol) of 2,2-bis(4-nitrobenzyl)malonic acid and 1.42 ml (10.7 mmol) 6-chlorohexanol were suspended in 5.0 ml toluene. 1.0 ml sulphuric acid are added. The reaction mixture was subsequently allowed to react for 21.5 hours at refluxing temperature. The reaction mixture was partitioned between water and ethyl acetate; the organic phase was washed repeatedly with water, dried over magnesium sulfate, filtered and concentrated by rotary evaporation. Chromatography of the residue on 150 g silica gel using toluene:ethyl acetate 19:1 as eluant yielded 0.94 g (78%) 6-chlorohexyl 2-(4 -nitrobenzyl)-3-(4-nitrophenyl)propanoate as yellow oil.

후처리

  1. customto react for 21.5 hours
  2. temperatureat refluxing temperature
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. washthe organic phase was washed repeatedly with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation

출처 및 근거

ORD 기록
ord-b20a33f19df04ea8be12e7cd97513ff7
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07994273B2

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