Water → (3-Methoxy-1,2-phenylene)dimethanol

HRID 1968764Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1968764
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[C:10](=[O:12])[O:9][CH2:8]2.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.C(Cl)Cl>C1COCC1>[OH:9][CH2:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:11]=1[CH2:10][OH:12]

Komponenten

6

Edukt 4

HCID 962Water2×HCID 6344DichloromethaneHCID 109865837-methoxy-3H-isobenzofuran-1-oneHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 14892485(3-Methoxy-1,2-phenylene)dimethanolAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 7-methoxy-3H-isobenzofuran-1-one (16.65 g, 101.4 mmol) in anhydrous THF (200 ml) was added at room temperature under an atmosphere of argon to a freshly prepared solution of LiAlH4 (7.70 g, 202.8 mmol, 2.0 equiv) in THF (100 ml). After 30 minutes at room temperature, TLC analysis indicated complete conversion. The reaction mixture was cooled to 0° C. and water was added dropwise until gas evolution ceased. Water (500 ml) and CH2Cl2 (500 ml) was added to form a white suspension. After filtration, the filtrate was extracted with CH2Cl2 (4 liters in total). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound (15.34 g, 90%) in adequate purity for direct use in the next transformation. 1H NMR (400 MHz, CDCl3): δ=7.27 (t, J=7.8 Hz, 1H), 6.96 (d, J=7.3 Hz, 1H), 6.89 (d, J=8.3 Hz, 1H), 4.83 (s, 2H); 4.72 (s, 2H), 3.85 (s, 3H), 2.8-2.6 (br s, 2H). MS (ES+): 169 (M+H)+.

Aufarbeitung

  1. customto form a white suspension
  2. filtrationAfter filtration
  3. extractionthe filtrate was extracted with CH2Cl2 (4 liters in total)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4a73947df006476db2b16a4441c820fa
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426440B2

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