Water → 4-Methoxybenzo[d][1,3]dioxole

HRID 1179224

Reaktionsgleichung

Reaktionsgleichung von HRID 1179224
[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. customs, 3H)HPLC (method A) 2.86 min.

Quellen und Nachweise

ORD-Eintrag
ord-b76f1394950c4580a504f32f244b457c
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279469B2

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