Diethyl Ether → 1,5-Dihydro-3-methoxy-2,4-benzodioxepin

HRID 50546

Reaktionsgleichung

Reaktionsgleichung von HRID 50546
C([CH:4]1[O:10][CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[CH2:6][O:5]1)=CC.C1(CO)C([CH2:21][OH:22])=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.CCOCC>COCCOC>[CH3:21][O:22][CH:4]1[O:5][CH2:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH2:9][O:10]1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 691531,2-BenzenedimethanolHCID 537201233-(1-propenyl)-1,5-dihydro-3H-2,4-benzodioxepine

Produkt 1

HCID 37952081,5-Dihydro-3-methoxy-2,4-benzodioxepinAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A method for synthesizing 3-(1-propenyl)-1,5-dihydro-3H-2,4-benzodioxepine is illustrated in Scheme 3. 1,2-Benzenedimethanol (500 mg, 3.62 mmol) and p-toluenesulfonic acid (172 mg, 0.9 mmol) were dissolved in 2 mL of dry DME and triethylortoformate (0.396 mL, 3.62 mmol) was added. The solution was stirred at rt. and under argon for 1 h. Ether (20 mL) was added and the organic layer washed with a saturated solution of NaHCO3 and water, then dried (Na2SO4). The solvent was evaporated giving crude 3-methoxy-1,5-dihydro-3H-2,4 benzodioxepine as a colorless oil (526 mg, 89%).

Aufarbeitung

  1. additiontriethylortoformate (0.396 mL, 3.62 mmol) was added
  2. washthe organic layer washed with a saturated solution of NaHCO3 and water
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-6acbabc4189d4bf5b0e7c53207e55958
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713287B1

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