(3,6-Dimethyl-1,2-phenylene)dimethanol → 4,7-Dimethyl-3H-isobenzofuran-1-one

HRID 1879525Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1879525
[OH:1][CH2:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([CH3:10])[C:4]=1[CH2:11][OH:12]>[O-2].[Mn+4].[O-2].ClCCl>[CH3:9][C:8]1[CH:7]=[CH:6][C:5]([CH3:10])=[C:4]2[C:3]=1[CH2:2][O:1][C:11]2=[O:12]

Komponenten

4

Edukt 1

HCID 13220177(3,6-Dimethyl-1,2-phenylene)dimethanol

Produkt 1

HCID 5839124,7-Dimethyl-3H-isobenzofuran-1-oneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 1 L 3-necked RBF is charged with 1,2-bis(hydroxymethyl)-3,6-dimethyl-benzene 3 (22.05 g, 0.133 mol), activated 85% manganese(IV) oxide (135.69 g, 1.327 mol), 4 Å molecular sieves (12.00 g) and anhydrous dichloromethane (500 mL), and placed under nitrogen. The reaction mixture is heated to reflux and stirred for 22 h. The reaction mixture is filtered through Kieselguhr and washed thoroughly with dichloromethane. The filtrate is concentrated in vacuo to yield the product 4 as a cream solid (19.79 g, 92%): 1H-NMR (300 MHz, CDCl3) δ 7.31 (d, 1H, 3J=7.5 Hz), 7.18 (d, 1H, 3J=7.5 Hz), 5.18 (s, 2H), 2.65 (s, 3H), 2.29 (s, 3H); 13C-NMR (75 MHz, CDCl3) δ 171.7, 145.8, 136.9, 134.5, 130.8, 129.3, 122.9, 68.3, 16.96, 16.91.

Aufarbeitung

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux
  3. filtrationThe reaction mixture is filtered through Kieselguhr
  4. washwashed thoroughly with dichloromethane
  5. concentrationThe filtrate is concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e7245aecc2e24e989bb4edf0e5e8c72e
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318048B2

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