Acetic Acid → HCID 178472486, Verbindung

HRID 271344Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271344
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.C(O)(=O)C.[H][H]>[Rh].C(O)C>[CH2:9]([O:8][C:6]([C@H:5]1[CH2:11][CH2:12][C@@H:2]([OH:1])[CH2:3][CH2:4]1)=[O:7])[CH3:10]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 8434EthylparabenHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 178472486HCID 178472486, VerbindungAusbeute 106,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23948RhodiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 10 g of ethyl 4-hydroxybenzoate, 5 mL of acetic acid, 0.8 g of 5% rhodium on alumina, and 200 mL of ethanol was shaken under 55 psi of hydrogen for 48 h, filtered and concentrated under reduced pressure. The residue was taken up in 200 mL of toluene and again concentrated under reduced pressure to remove acetic acid. Drying under vacuum overnight gave 11 g of product, which was predominantly cis (83:17 cis: trans by HPLC), as a colorless oil: MS (m+1)=173.2; 1H NMR (400 MHz, CDCl3) 4.1 (dd, 2H), 3.9 (m, cis isomer, 0.85H), 3.6 (m, trans isomer, 0.15H), 2.4 and 2.2 (m, 1H), 2.0 (m, 2H), 1.62 (m, 6H), 1.2 (t, 3H).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. concentrationagain concentrated under reduced pressure
  4. customto remove acetic acid
  5. customDrying under vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-3ca0c3b196a44368890c7a7d69b34294
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452893B2

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