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Benzoyl chloride → HCID 13318174, Verbindung

HRID 1262816
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1262816
[CH3:1][C:2]1[C:6]([OH:7])=[C:5]([C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])[S:4][C:3]=1[C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15].C(N(CC)CC)C.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O1CCOCC1>[CH3:1][C:2]1[C:6]([O:7][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:5]([C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])[S:4][C:3]=1[C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 54703303HCID 54703303, Verbindung

Produkt 1

HCID 13318174HCID 13318174, VerbindungAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

A mixture of di-isopropyl 3-methyl-4-hydroxy-2,5-thiophene-dicarboxylate (656 g, 2.30 mol), triethylamine (297 g, 2.98 mol) and dioxane (2 l) was cooled with ice to about 10° C. The solution was added, while stirring, with benzoyl chloride (351 g, 2.5 mol) over about 10 minutes, followed by further stirring for 30 minutes at room temperature. After removing the precipitate of triethylamine hydrochloride salt by filtration, the solution was distilled in vacuo to remove dioxane. Toluene was then added to the remaining residue, and the solution was washed with 5% aqueous sodium bicarbonate and water, and then dried over MgSO4. The solvent was removed by distillation to give almost pure di-isopropyl 3-methyl-4-benzoyloxy-2,5-thiophene dicarboxylate (851 g, 95%). nD10 1.5499.

Aufarbeitung

  1. additionThe solution was added
  2. customAfter removing the precipitate of triethylamine hydrochloride salt
  3. filtrationby filtration
  4. distillationthe solution was distilled in vacuo
  5. customto remove dioxane
  6. additionToluene was then added to the remaining residue
  7. washthe solution was washed with 5% aqueous sodium bicarbonate and water
  8. dry with materialdried over MgSO4
  9. customThe solvent was removed by distillation

Quellen und Nachweise

ORD-Eintrag
ord-ce623c9f9d4e478eb4717369f83e9235
Quelldatensatz
uspto-grants-1984_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04454131

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