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Methanol → HCID 13134408、化合物

HRID 1444420
ノート
印刷プレビュー

反応式

HRID 1444420 の反応式
[CH3:1][O:2][C:3](=[O:21])[CH:4]([C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19])C(OC)=O.Cl(O)(=O)(=O)=O.C(OCC)(=O)C.CO>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19]
参加物反応条件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 887MethanolHCID 8857Ethyl AcetateHCID 24247Perchloric AcidHCID 13134407Dimethyl (2,6-dinitrophenyl)propanedioate

生成物 1

HCID 13134408HCID 13134408、化合物収率 89%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
125 °C

実験手順

10.08 g (33.8 mmol) of dimethyl-2-(2,6-dinitrophenyl)-malonate is mixed in 54 ml of glacial acetic acid with 2.7 ml of perchloric acid and refluxed at 125° C. In this case, the ethyl acetate that is produced is distilled off. After 90 minutes, the reaction is brought to a halt, since starting material is no longer present according to TLC. The reaction mixture is poured into ice water and extracted three times with ethyl acetate. The combined organic extracts are shaken with 5% sodium bicarbonate solution, with water and with brine. After the organic phase is dried, the desiccant is filtered off and the solvent is spun off, a residue remains that is chromatographed on silica gel (mobile solvent ethyl acetate/hexane). 4.69 g of the (2,6-dinitrophenyl)-acetic acid, which then is esterified with methanol (16 ml) and concentrated sulfuric acid (0.4 ml), is isolated. To this end, the acid and the reagents are refluxed for seven hours. The methanol is spun off, and the residue is worked up in the usual way. After chromatography on silica gel (mobile solvent ethyl acetate/hexane), 4.43 g (89%) of the desired ester is obtained.

後処理

  1. distillationis distilled off
  2. additionThe reaction mixture is poured into ice water
  3. extractionextracted three times with ethyl acetate
  4. customAfter the organic phase is dried
  5. filtrationthe desiccant is filtered off
  6. customthat is chromatographed on silica gel (mobile solvent ethyl acetate/hexane)
  7. customis isolated
  8. temperatureTo this end, the acid and the reagents are refluxed for seven hours

出典と根拠

ORDレコード
ord-c2159f4110fa47fe981d5d32e2f76cd5
出典データセット
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07662821B2

反応ノート

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