1,4-Benzenedimethanol → 1,2-Benzenedimethanol

HRID 525639

Reaktionsgleichung

Reaktionsgleichung von HRID 525639
[C:1]1(CO)[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.C(O)(=O)CC[C:14](C)=[O:15].C(N=C=NC(C)C)(C)C>CN(C1C=CN=CC=1)C.ClCCl>[C:3]1([CH2:14][OH:15])[C:4]([CH2:7][OH:8])=[CH:5][CH:6]=[CH:1][CH:2]=1

Komponenten

6

Edukt 3

HCID 115061,4-BenzenedimethanolHCID 11579Levulinic AcidHCID 12734Diisopropylcarbodiimide

Produkt 1

HCID 691531,2-BenzenedimethanolAusbeute 191 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a flask with dichloromethane (ca. 25 ml), 1,4-phenylenedimethanol (5 g, 0.036 mol) and levulinic acid (8.36 g, 0.072 mol) were mixed. The flask was then cooled in an ice water bath. Diisopropyl carbodiimide (9.09 g, 0.072 mol) and the catalyst DMAP (ca. 100 mg) were then added slowly to the solution. The mixture was allowed to come to room temperature and was stirred overnight. The mixture was then filtered and washed with 1M HCL brine. It was then dried over MgSO4 and concentrated in vacuo to afford a white solid as the product (9.5 g). Its purity was ascertained using 1H NMR (300 MHZ in CDCL3): δ 7.34 (s, 4H), 5.11 (s, 4H), 2.77 (t, 4H), 2.62 (t, 4H), 2.18 (s, 6H).

Aufarbeitung

  1. temperatureThe flask was then cooled in an ice water bath
  2. customto come to room temperature
  3. filtrationThe mixture was then filtered
  4. washwashed with 1M HCL brine
  5. dry with materialIt was then dried over MgSO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8f81c57c43cd473db1297008907b262d
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340658B2

Verknüpfte Notizen

Wird geladen…