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Acetic Anhydride → 1,2-Dimethyl 4,5-dimethyl-1,2-benzenedicarboxylate

HRID 596547
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 596547
[CH3:1][O:2][C:3](=[O:16])[CH:4]1[C:13](C)=[C:12]([CH3:15])[CH2:11][CH:10]=[C:5]1[C:6]([O:8][CH3:9])=[O:7].[Se](=O)=O.[C:20](OC(=O)C)(=O)C>C(Cl)Cl>[CH3:9][O:8][C:6](=[O:7])[C:5]1[C:4](=[CH:13][C:12]([CH3:15])=[C:11]([CH3:20])[CH:10]=1)[C:3]([O:2][CH3:1])=[O:16]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7918Acetic Anhydride2×HCID 24007Selenium DioxideHCID 536587435,6 Dimethyl-1,4-dihydro-phthalic acid dimethyl ester

Produkt 1

HCID 6058061,2-Dimethyl 4,5-dimethyl-1,2-benzenedicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

232 parts of the 5,6-dimethyl-1,4-dihydro-phthalic acid dimethyl ester (I) obtained in A) are first freed from readily volatile constituents in vacuo and then diluted with 400 parts by volume of acetic anhydride. Then 133 parts of selenium dioxide are slowly added by small amounts to the reaction mixture, which is heated to 100° C, and the temperature rises to 130° C without external application of heat. The reaction mixture is subsequently refluxed for 3 hours and freed from acetic anhydride in vacuo. The residue is taken up in methylene chloride, the solution is freed from precipitated selenium by filtration, then freed from acid constituents with a saturated aqueous sodium bicarbonate solution, washed neutral with water, dried over sodium sulphate and concentrated to dryness in vacuo. Yield: 230 parts of a yellowish brown oil which a gas chromatogram shows to have a 94% content of 4,5-dimethyl-phthalic acid dimethyl ester (II). The product is distilled under a high vacuum. The fraction with a boiling range of 116°-120° C (0.04 Torr) contains 174 parts (78% of theory) of 4,5-dimethyl-phthalic acid dimethyl ester (II) with a melting point of 54°-55° C.

Aufarbeitung

  1. customrises to 130° C without external application
  2. temperatureof heat
  3. temperatureThe reaction mixture is subsequently refluxed for 3 hours
  4. customfrom precipitated selenium
  5. filtrationby filtration
  6. washwashed neutral with water
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated to dryness in vacuo
  9. distillationThe product is distilled under a high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-903e21612c1f425d9969597fde69ae33
Quelldatensatz
uspto-grants-1977_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04011261

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