Nitric Acid → 5-[2-(3-Chloro-phenyl)-ethoxy]-4-methoxy-2-nitro-benzoic acid methyl ester

HRID 521455ノート

反応式

HRID 521455 の反応式
OC1C=C(C=CC=1OC)C(OC)=O.ClC1C=C(CCO)C=CC=1.[CH3:24][O:25][C:26](=[O:45])[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[CH:39]=2)[CH:28]=1.[N+:46]([O-])([OH:48])=[O:47]>>[CH3:24][O:25][C:26](=[O:45])[C:27]1[CH:28]=[C:29]([O:35][CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[CH:39]=2)[C:30]([O:33][CH3:34])=[CH:31][C:32]=1[N+:46]([O-:48])=[O:47]

参加物

5

反応物 4

HCID 944Nitric AcidHCID 78856m-Chlorophenethylic alcoholHCID 4056967Methyl 3-hydroxy-4-methoxybenzoateHCID 670762963-[2-(3-Chloro-phenyl)-ethoxy]-4-methoxy-benzoic acid methyl ester

生成物 1

HCID 670767915-[2-(3-Chloro-phenyl)-ethoxy]-4-methoxy-2-nitro-benzoic acid methyl ester

実験手順

Methyl 3-hydroxy-4-methoxybenzoate and 2-(3-chlorophenyl)-ethanol were reacted in analogy to step 1 of example 1. The obtained 3-[2-(3-chloro-phenyl)-ethoxy]-4-methoxy-benzoic acid methyl ester (0.750 g, 2.34 mmol) was added slowly to ice-cooled 100% nitric acid (10 ml). The ice bath was removed and stirring was continued overnight. The mixture was cautiously transferred into a stirred mixture of EA, water and an excess of sodium hydrogencarbonate and extracted with EA. The combined organic extracts were washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated to dryness. The solid residue was extracted with diethyl ether, and the ethereal solution was evaporated. The residue was stirred with HEP, and the solid was filtered and dried in vacuo to give 0.680 g of the title compound.

後処理

  1. customThe ice bath was removed
  2. additionThe mixture was cautiously transferred into a stirred mixture of EA, water
  3. extractionan excess of sodium hydrogencarbonate and extracted with EA
  4. washThe combined organic extracts were washed with a saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. extractionThe solid residue was extracted with diethyl ether
  9. customthe ethereal solution was evaporated
  10. stirringThe residue was stirred with HEP
  11. filtrationthe solid was filtered
  12. customdried in vacuo

出典と根拠

ORDレコード
ord-fc3fa8a1cef34d83aa89e4341f66f39d
出典データセット
uspto-grants-2016_05
特許番号
US09328071B2

反応ノート

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