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Hydrochloric Acid → 6-[((2E)-{4-hydroxyphenyl}prop-2-enoyl)oxy]hexyl 3,5-dinitrobenzoate

HRID 1922545
ノート
印刷プレビュー

反応式

HRID 1922545 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:33]=[C:34]([N+:36]([O-:38])=[O:37])[CH:35]=1)[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17](=[O:32])/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23]([O:26]C(OCC)=O)=[CH:22][CH:21]=1)=[O:8])([O-:3])=[O:2].N1C=CC=CC=1.[OH-].[NH4+].Cl>CC(C)=O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:33]=[C:34]([N+:36]([O-:38])=[O:37])[CH:35]=1)[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17](=[O:32])/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)=[O:8])([O-:3])=[O:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 14923Ammonium HydroxideHCID 598504176-[((2E)-{4-[(ethoxycarbonyl)oxy]phenyl}prop-2-enoyl)oxy]hexyl 3,5-dinitrobenzoate

生成物 1

HCID 598504266-[((2E)-{4-hydroxyphenyl}prop-2-enoyl)oxy]hexyl 3,5-dinitrobenzoate収率 42.7%

試薬・触媒・溶媒 1

HCID 180
Acetone
溶媒

実験手順

43.20 g (0.081 Mol) of 6-[((2E)-{4-[(ethoxycarbonyl)oxy]phenyl}prop-2-enoyl)oxy]hexyl 3,5-dinitrobenzoate are dissolved in 66 ml (0.815 Mol) of pyridine and 400 ml of acetone at room temperature. 61 ml (0.815 Mol) of ammonium hydroxide solution 25% are added dropwise to the solution at room temperature. After 12 h reaction, the mixture is thrown on water and acidified by the addition of HCl 25% (up to pH=3-4). A paste is obtained which is filtrated and dissolved in ethyl acetate and extracted with water. The organic phase is dried with sodium sulfate, filtrated, concentrated by rotary evaporation. Filtration of the residue over silica gel with tert-Butyl methyl ether as eluant and crystallization of the residue in 200 ml of ethyl acetate and 1200 ml of hexane at 0° C. give 15.84 g of 6-[((2E)-{4-hydroxyphenyl}prop-2-enoyl)oxy]hexyl 3,5-dinitrobenzoate as yellow crystals.

後処理

  1. customat room temperature
  2. customAfter 12 h reaction
  3. customA paste is obtained which
  4. filtrationis filtrated
  5. dissolutiondissolved in ethyl acetate
  6. extractionextracted with water
  7. dry with materialThe organic phase is dried with sodium sulfate
  8. filtrationfiltrated
  9. concentrationconcentrated by rotary evaporation
  10. filtrationFiltration of the residue over silica gel with tert-Butyl methyl ether as eluant
  11. customcrystallization of the residue in 200 ml of ethyl acetate

出典と根拠

ORDレコード
ord-8ce9efdd3c954a1cab06995231b7029d
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08173749B2

反応ノート

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