HCID 22452664, Verbindung → HCID 22452628, Verbindung

HRID 2185905Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2185905
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C:15]([OH:17])=[O:16])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)([CH3:3])[CH3:2]>CC(O)=O.[Pd]>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C:15]([OH:17])=[O:16])[C:8]2[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=2[CH:14]=1)([CH3:3])[CH3:2]

Komponenten

4

Edukt 1

HCID 22452664HCID 22452664, Verbindung

Produkt 1

HCID 22452628HCID 22452628, VerbindungAusbeute 100,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 3-(isopropoxy)-1-naphthalenecarboxylic acid (0.38 g, 1.65 mmol) and 10% Pd/C (0.10 g) in HOAc (20 mL) was hydrogenated on Parr apparatus at 60° C. and 50 psi for 13 h. After filtration through diatomaceous earth the solvent was removed in vacuo, water was added and the precipitate was extracted into EtOAc. The combined organic layers were dried (MgSO4), filtered and concentrated to yield the title acid as a light yellow oil (0.39 g, 100%). 1H NMR (CDCl3) δ 7.39 (d, 1H), 6.83 (d, 1H), 4.55 (m, 1H), 3.02 (s, 2H), 2.80 (s, 2H), 1.77 (m, 4H), 1.34 (s, 3H), 1.32 (s, 3H); MS m/z 233 (M−H).

Aufarbeitung

  1. customwas hydrogenated on Parr apparatus at 60° C.
  2. filtrationAfter filtration through diatomaceous earth the solvent
  3. customwas removed in vacuo, water
  4. additionwas added
  5. extractionthe precipitate was extracted into EtOAc
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-393d04bbbaa14af7be5f1b6adc18c252
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06403601B1

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