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Hydrochloric Acid → 2-Cyano-2-(2-nitro-5-phenoxy-benzyl)-hex-5-enoic acid

HRID 252461
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 252461
C([O:3][C:4](=[O:29])[C:5]([C:27]#[N:28])([CH2:10][C:11]1[CH:16]=[C:15]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=[CH:13][C:12]=1[N+:24]([O-:26])=[O:25])[CH2:6][CH2:7][CH:8]=[CH2:9])C.[Li+].[OH-].Cl>CO.O>[C:27]([C:5]([CH2:10][C:11]1[CH:16]=[C:15]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=[CH:13][C:12]=1[N+:24]([O-:26])=[O:25])([CH2:6][CH2:7][CH:8]=[CH2:9])[C:4]([OH:29])=[O:3])#[N:28]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 574757172-Cyano-2-(2-nitro-5-phenoxy-benzyl)-hex-5-enoic acid ethyl ester2×

Produkt 1

HCID 574757182-Cyano-2-(2-nitro-5-phenoxy-benzyl)-hex-5-enoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel
HCID 962
Water
Lösungsmittel

Versuchsvorschrift

2-cyano-2-(2-nitro-5-phenoxy-benzyl)-hex-5-enoic acid ethyl ester (2.84 g, 7.20 mmol) was dissolved in methanol (42 mL). In a separate flask, LiOH (1.5 g, 36.0 mmol) was dissolved in water (21 mL). The LiOH solution was added to the methanolic solution containing 2-cyano-2-(2-nitro-5-phenoxy-benzyl)-hex-5-enoic acid ethyl ester and the reaction was allowed to stir at room temperature for 2 hours. Next, 12N HCl (3 mL) was added to the reaction mixture followed by removal of the methanol under reduced pressure. The reaction mixture was poured into a separatory funnel, ethyl acetate was added and the organic layer was washed 2 times with 1N HCl and one time with saturated brine solution. The organic layer was separated, dried with sodium sulfate, filtered and the solvent was removed to yield a residue.

Aufarbeitung

  1. customfollowed by removal of the methanol under reduced pressure
  2. additionThe reaction mixture was poured into a separatory funnel
  3. additionethyl acetate was added
  4. washthe organic layer was washed 2 times with 1N HCl and one time with saturated brine solution
  5. customThe organic layer was separated
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was removed
  9. customto yield a residue

Quellen und Nachweise

ORD-Eintrag
ord-86cdbd217273482495a31a1f2f22d7f1
Quelldatensatz
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07868022B2

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