Hydrochloric Acid → 14-Hydroxytetradecanoic acid

HRID 1526755

Reaktionsgleichung

Reaktionsgleichung von HRID 1526755
[OH-].[K+].C([O:7][C:8](=[O:23])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])(C)(C)C.Cl>O.CO>[OH:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]([OH:23])=[O:7]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 42636661Tert-butyl 14-hydroxytetradecanoate

Produkt 1

HCID 308427614-Hydroxytetradecanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of potassium hydroxide (8.60 g, 153 mmol) in water (100 mL) was added to a solution of the above ester (9.20 g, 30.6 mmol) in methanol (100 mL) and the resulting mixture was heated at 60 C for 2 days. The mixture was cooled to room temperature; then it was washed with hexanes (2×70 mL) and concentrated in vacuo. Concentrated hydrochloric acid (32%, 20 mL, 0.65 mol) was added dropwise and the mixture was extracted with ethyl acetate (2×150 mL). The combined organic layers were dried over anhydrous magnesium sulfate and evaporated to dryness to yield 14-hydroxy-tetradecanoic acid as white solid.

Aufarbeitung

  1. temperaturethe resulting mixture was heated at 60 C for 2 days
  2. washthen it was washed with hexanes (2×70 mL)
  3. concentrationconcentrated in vacuo
  4. extractionthe mixture was extracted with ethyl acetate (2×150 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-8317522b3c9e4bfda0b3be4b6dbbfdf7
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085637B2

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