Ethyl Acetate → 2,3-Dihydrothieno(3,4-b)-1,4-dioxin-2-methanol

HRID 489588

Reaktionsgleichung

Reaktionsgleichung von HRID 489588
[OH:1][CH2:2][CH:3]1[O:8][C:7]2=[C:9](C(O)=O)[S:10][C:11](C(O)=O)=[C:6]2[O:5][CH2:4]1.C(OCC)(=O)C>CN(C)C(=O)C.N1C2C(=CC=CC=2)C=CC=1>[O:8]1[CH:3]([CH2:2][OH:1])[CH2:4][O:5][C:6]2=[CH:11][S:10][CH:9]=[C:7]12

Komponenten

5

Edukt 2

HCID 8857Ethyl AcetateHCID 219583572-Hydroxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid

Produkt 1

HCID 160674382,3-Dihydrothieno(3,4-b)-1,4-dioxin-2-methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7047QuinolineKatalysatorHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

2-Hydroxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid (48 g, 0.184 mol) was dissolved in N,N-dimethylacetamide (500 mL), and Cu2Cr2O7 (8.6 g) and quinoline (15 drops) were added. This mixture was subsequently stirred for 2 hours at 150° C., after which it was cooled to 25° C. It was then poured into ethyl acetate, the catalyst was removed by filtration and the filtrate was washed with acidic water and aqueous, saturated NaCl. Subsequently, the solvent was removed after which pure (2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-yl)-methanol was isolated by vacuum distillation (115-120° C.; 0.05 mm Hg).

Aufarbeitung

  1. temperatureafter which it was cooled to 25° C
  2. customthe catalyst was removed by filtration
  3. washthe filtrate was washed with acidic water
  4. customSubsequently, the solvent was removed after which pure (2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-yl)-methanol
  5. customwas isolated by vacuum distillation (115-120° C.; 0.05 mm Hg)

Quellen und Nachweise

ORD-Eintrag
ord-4e91a7b2b6004e24aa5027f1d3b8ca0c
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06977390B2

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