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Hydrochloric Acid → Benzyl 2-benzyloxy-5-cyanobenzoate

HRID 644400
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 644400
[CH2:1]([O:8][C:9](=[O:26])[C:10]1[CH:15]=[C:14]([CH:16]=O)[CH:13]=[CH:12][C:11]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.NO.C[N:31]1CCCC1=O.Cl>O>[CH2:1]([O:8][C:9](=[O:26])[C:10]1[CH:15]=[C:14]([C:16]#[N:31])[CH:13]=[CH:12][C:11]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 443297Hydroxyamine hydrochlorideHCID 10405334Benzyl 2-benzyloxy-5-formylbenzoate

Produkt 1

HCID 18974028Benzyl 2-benzyloxy-5-cyanobenzoateAusbeute 76,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

A mixture of 2-benzyloxy-5-formylbenzoic acid benzyl ester (693 mg, 2 mmol), hydroxylamine hydrochloride (167 mg, 2.4 mmol), and N-methylpyrrolidone (3 mL) was stirred at 115□ for 4 hours. After the reaction mixture was cooled, 2N hydrochloric acid (5 mL) and water (30 mL) were added and the mixture was extracted with ethyl acetate. The organic layer was washed with 2N aqueous sodium hydroxide, water, and brine, and dried over anhydrous magnesium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was suspended and washed with isopropyl ether under heating at reflux to give the title compound (527 mg, 76.7%) as a white solid.

Aufarbeitung

  1. temperatureAfter the reaction mixture was cooled
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with 2N aqueous sodium hydroxide, water, and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe residue obtained by evaporation of the solvent under reduced pressure
  6. washwashed with isopropyl ether
  7. temperatureunder heating
  8. temperatureat reflux

Quellen und Nachweise

ORD-Eintrag
ord-8f6971dc03a5490c9bc034032685815f
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07700655B2

Notizen zur Reaktion

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