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

HRID 1671536ノート

反応式

HRID 1671536 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b20a33f19df04ea8be12e7cd97513ff7
出典データセット
uspto-grants-2011_08
特許番号
US07994273B2

反応ノート

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