Hydrochloric Acid → 3-(4-Hydroxyphenyl)hex-4-ynoic acid

HRID 390387

Reaktionsgleichung

Reaktionsgleichung von HRID 390387
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]2C(=O)OC(C)(C)[O:14][C:13]2=[O:21])[C:9]#[C:10][CH3:11])=[CH:4][CH:3]=1.Cl>N1C=CC=CC=1.O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:9]#[C:10][CH3:11])[CH2:12][C:13]([OH:21])=[O:14])=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 598551335-(1-(4-Hydroxyphenyl)but-2-yn-1-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Produkt 1

HCID 598551363-(4-Hydroxyphenyl)hex-4-ynoic acidAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 66926435Pyridine waterLösungsmittel

Versuchsvorschrift

A solution of 5-[1-(4-hydroxyphenyl)but-2-ynyl]-2,2-dimethyl-1,3-dioxane-4,6-dione (20 g, 69.44 mmol) in pyridine-water (5:1, 390 mL) is heated at reflux for 16 hours and after cooling is acidified to pH ˜2 with 5 N HCl and extracted with EtOAc (2×300 mL). The combined extracts are washed with saturated brine, dried over MgSO4, filtered, and concentrated to give an off-white solid (13.5 g, 96%). ESI/MS m/z 203 (M−H)−.

Aufarbeitung

  1. temperatureat reflux for 16 hours
  2. temperatureafter cooling
  3. extractionextracted with EtOAc (2×300 mL)
  4. washThe combined extracts are washed with saturated brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-45f98b47da3b415db8f3f616c25e4520
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383642B2

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