Pyridine → 1,2-Benzenedimethanol

HRID 525638

Reaktionsgleichung

Reaktionsgleichung von HRID 525638
[C:1]1(CO)[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.N1C=CC=CC=1.ClCCl.[C:20](Cl)(=[O:24])C(C)C>CN(C1C=CN=CC=1)C.[Cl-].[Na+].O>[C:3]1([CH2:20][OH:24])[C:4]([CH2:7][OH:8])=[CH:5][CH:6]=[CH:1][CH:2]=1

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 115061,4-BenzenedimethanolHCID 62325Isobutyryl chloride

Produkt 1

HCID 691531,2-BenzenedimethanolAusbeute 212,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

1,4-xylylene glycol (5 g, 0.0306 mol), pyridine (5.7 g, 0.072 mol), and catalyst DMAP (ca. 100 mg) in a solution of dichloromethane (ca. 25 ml) were added to a flask. Isobutyryl chloride (7.71 g, 0.072 mol) was then added to the solution drop wise. The mixture was stirred overnight. 1M HCL brine was used to wash the mixture. The organic layer was dried over MgSO4 and concentrated in vacuo to afford a clear oil as the product (9 g). Its purity was ascertained using 1H NMR (300 MHz in CDCL3): δ 7.34 (s, 4H), 5.11 (s, 4H), 2.60 (sept, 2H), 1.19 (d, 12H).

Aufarbeitung

  1. washto wash the mixture
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-709dbd25a92f41c0adc014e5dfe877dd
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340658B2

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