5-(4-Benzyloxy-benzyl)-2,2-dimethyl-[1,3]dioxolan-4-one → 5-(4-Hydroxy-benzyl)-2,2-dimethyl-(1,3]dioxolan-4-one

HRID 1985260Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1985260
C([O:8][C:9]1[CH:23]=[CH:22][C:12]([CH2:13][CH:14]2[O:18][C:17]([CH3:20])([CH3:19])[O:16][C:15]2=[O:21])=[CH:11][CH:10]=1)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[OH:8][C:9]1[CH:23]=[CH:22][C:12]([CH2:13][CH:14]2[O:18][C:17]([CH3:20])([CH3:19])[O:16][C:15]2=[O:21])=[CH:11][CH:10]=1

Komponenten

4

Edukt 1

HCID 184437075-(4-Benzyloxy-benzyl)-2,2-dimethyl-[1,3]dioxolan-4-one

Produkt 1

HCID 99208865-(4-Hydroxy-benzyl)-2,2-dimethyl-(1,3]dioxolan-4-oneAusbeute 105 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 5-(4-benzyloxy-benzyl)-2,2-dimethyl-[1,3]dioxolan-4-one (1.0 g, 3.20 mmol) and 10% Pd/C (0.75 g) in EtOAc (40 mL) was purged with N2 then H2 and then stirred under a H2 balloon atmosphere for 3 h at room temperature. Upon reaction completion, Na2SO4 was added and the mixture filtered through hyflo. The solvent was removed in vacuo to afford 0.747 g (100%) 5-(4-hydroxy-benzyl)-2,2-dimethyl-[1,3]dioxolan-4-one. 1H NMR (500 MHz, CDCl3) δ 7.11 (d, 2H, J=8.31 Hz), 6.76 (d, 2H, J=8.31 Hz), 4.92 (bs, 1H), 4.61 (dd, 1H, J=6.36 Hz, J=4.40 Hz), 3.11 (dd, 1H, J=14.67 Hz, J=4.40 Hz), 2.98 (dd, 1H, J=14.67 Hz, J=4.40 Hz), 1.50 (s, 3H), 1.36 (s, 3H); MS (ES−) Calc'd for C12H13O4 (M−1) 221. Found m/z 221 (100%).

Aufarbeitung

  1. customwas purged with N2
  2. customUpon reaction completion, Na2SO4
  3. additionwas added
  4. filtrationthe mixture filtered through hyflo
  5. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-56ad272342a54266ba68b859f9e8e32b
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544812B2

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