Hydrochloric Acid → 4-(3-Bromophenoxy)butanoic acid

HRID 84403Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 84403
[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][CH2:6][CH2:7][CH2:8][C:9]([O:11]CC)=[O:10].O.Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 22407915Ethyl 4-(3-bromophenoxy)butanoate

Produkt 1

HCID 23844144-(3-Bromophenoxy)butanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Ethyl 4-(3-bromophenoxy)butanoate 6 from Example 5 was taken up in 100 mL THF and 50 mL water and treated with lithium hydroxide LiOH (hydrate, 4.9 g). The whole was heated at 50° C. for 2 days. The mixture was cooled to room temperature and acidified to pH 1 with 2N HCl. The aqueous was extracted with ethylacetate. The combined organics were washed with brine and dried over sodium sulfate to give crude 4-(3-Bromophenoxy)butanoic acid 7 as a sticky solid. 1H NMR (DMSO-d6, 500 MHz) 7.24 (m, 1H), 7.13 (m, 1H), 7.11 (m, 1H), 6.95 (m, 1H), 3.99 (m, 2H), 2.37 (m, 2H), 1.94 (m, 2H).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe aqueous was extracted with ethylacetate
  3. washThe combined organics were washed with brine
  4. dry with materialdried over sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-35278bb27f7246b3ae6e77d2275fa513
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846762B2

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