3-Hydroxy-5-(3-benzyloxyphenyl)cyclohex-2-en-1-one → 3-Hydroxy-5-(3-hydroxyphenyl)cyclohex-2-en-1-one

HRID 703374Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 703374
[OH:1][C:2]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14]CC3C=CC=CC=3)[CH:9]=2)[CH2:5][C:4](=[O:22])[CH:3]=1>C(O)C.[Pd]>[OH:1][C:2]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[CH:9]=2)[CH2:5][C:4](=[O:22])[CH:3]=1

Komponenten

4

Edukt 1

HCID 221498233-Hydroxy-5-(3-benzyloxyphenyl)cyclohex-2-en-1-one

Produkt 1

HCID 200622803-Hydroxy-5-(3-hydroxyphenyl)cyclohex-2-en-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 20 g (0.068 mol) of 3-hydroxy-5-(3-benzyloxyphenyl)cyclohex-2-en-1-one in 250 mL of absolute ethanol was treated with 7.5 g of 5.0 percent palladium on carbon and shaken in a Parr® hydrogenator under 50 pounds of hydrogen pressure for 2 hours at room temperature. The reaction mixture was filtered through diatomaceous earth, diluted with 1 L of water and extracted thrice with 100 mL portions of ethyl acetate. The combined extracts were washed with an aqueous saturated NaCl solution, dried over MgSO4, filtered, concentrated and cooled to precipitate the desired above named product as a greyish-white solid in a yield of 9.8 g (71 percent of theoretical). The product melted at 140°-150° C./dec.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. additiondiluted with 1 L of water
  3. extractionextracted thrice with 100 mL portions of ethyl acetate
  4. washThe combined extracts were washed with an aqueous saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. temperaturecooled
  9. customto precipitate the

Quellen und Nachweise

ORD-Eintrag
ord-36ec401b53eb47c8bff7f7f59ac294dd
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04983211

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