Water → 4-Methoxybenzo[d][1,3]dioxole

HRID 601016

Reaktionsgleichung

Reaktionsgleichung von HRID 601016
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([OH:9])[C:4]=1[OH:10].Br[CH2:12]Cl.O>CN(C=O)C>[CH3:1][O:2][C:3]1[C:4]2[O:10][CH2:12][O:9][C:5]=2[CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 6333BromochloromethaneHCID 136223-Methoxycatechol

Produkt 1

HCID 5924784-Methoxybenzo[d][1,3]dioxole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 3-methoxy-benzene-1,2-diol (1.161 g, 8.28 mmol) in DMF (10 mL) was added to bromo-chloro-methane (611 ul, 1.1 equivalents) and stirred at 90 degrees Celsius for 4 hours. The mixture was poured into water and extracted with dichloromethane. The organic layer was poured thru a phase separator cartridge and concentrated to dryness. The crude product is a yellow liquid. The liquid was purified by column chromatography yielding 1.21 g, (96%). 1H-NMR (DMSO, 500 MHz) 6.7 (t, 1H), 6.63 (d, 1H), 6.58 (d, 1H), 5.97 (s, 2H), 3.83 (s, 3H) HPLC (method A) 2.86 min.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. additionThe organic layer was poured thru a phase separator cartridge
  3. concentrationconcentrated to dryness
  4. customThe liquid was purified by column chromatography
  5. customyielding 1.21 g, (96%)
  6. custom1H-NMR (DMSO, 500 MHz) 6.7 (t, 1H), 6.63 (d, 1H), 6.58 (d, 1H), 5.97 (s, 2H), 3.83 (s, 3H) HPLC (method A) 2.86 min.

Quellen und Nachweise

ORD-Eintrag
ord-8b088c76980d4f5fa34226426361b0f4
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902239B2

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