Sodium Sulfite → 4-[2-Ethoxy-2-(2,2,2-trichloro-ethoxy carbonyl)-ethyl]-benzoic acid

HRID 1628159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628159
[Cl:1][C:2]([Cl:21])([Cl:20])[CH2:3][O:4][C:5](=[O:19])[CH:6]([O:16][CH2:17][CH3:18])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=1.[O-:22][Mn](=O)(=O)=O.[K+].[O-]S([O-])=O.[Na+].[Na+]>CC(C)=O.CCOC(C)=O.Cl>[CH2:17]([O:16][CH:6]([C:5]([O:4][CH2:3][C:2]([Cl:20])([Cl:21])[Cl:1])=[O:19])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:22])=[O:15])=[CH:10][CH:9]=1)[CH3:18]

Komponenten

7

Edukt 3

HCID 24437Sodium SulfiteHCID 516875Potassium PermanganateHCID 668648052-Ethoxy-3-(4-hydroxymethyl-phenyl)-propionic acid 2,2,2-trichloroethyl ester

Produkt 1

HCID 668653064-[2-Ethoxy-2-(2,2,2-trichloro-ethoxy carbonyl)-ethyl]-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 313Hydrochloric AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Ethoxy-3-(4-hydroxymethyl-phenyl)-propionic acid 2,2,2-trichloroethyl ester (0.044 g, 0.125 mmol) was dissolved in acetone (3 mL) and KMnO4 (0.039 g, 0.247 mmol) was added and the purple solution was stirred for 4 h at room temperature. Saturated aq. Na2SO3 solution was added and after 2 min. stirring, the mixture was diluted with EtOAc and aq. HCl (2N) resulting in two clear and colorless phases. The organic layer was separated and dried (MgSO4) and evaporated to afford the desired carboxylic acid which was proceeded on to the next step without further purification (0.034 g, 75%). 1H NMR (400 MHz, CDCl3): δ 8.01-8.03 (d, 2H), 7.36-7.38 (d, 2H), 4.73-4.83 (q, 2H), 4.15-4.18 (m, 1H), 3.65-3.69 (m, 1H), 3.33-3.37 (m, 1H), 3-07-3.20 (m, 2H), 1.14 (t, 3H).

Aufarbeitung

  1. stirringstirring
  2. customresulting in two clear
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ff1300579fd746a8a249cc1c75a5cc36
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785681B2

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