Dimethyl terephthalate → Didocosyl terephthalate

HRID 400312

Reaktionsgleichung

Reaktionsgleichung von HRID 400312
[C:1]([O:13][CH3:14])(=[O:12])[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C(O)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>CO>[C:6]([O:8][CH2:9][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH3:16])(=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([C:1]([O:13][CH2:14][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH3:16])=[O:12])=[CH:3][CH:4]=1

Komponenten

4

Edukt 2

HCID 8441Dimethyl terephthalateHCID 12620Behenyl Alcohol

Produkt 1

HCID 19821458Didocosyl terephthalateAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To a 3 neck 500 mL round bottomed flask equipped with a Dean Stark trap and condenser, thermocouple and argon inlet was added dimethyl terephthalate (49.57 grams, available from Sigma Aldrich), 1-docosanol (167.76 grams, available from Spectrum Chemical), Fascat 4100 (0.22 grams, available from Arkema Inc) and Xylenes (100 mL, available from Sigma Aldrich). The mixture was slowly heated under argon to 160° C. during which reagents melted. The temperature was raised to 180° C. The reaction mixture was stirred at 180° C. overnight (about 20 hours) during which 63 mL of a mixture of xylenes and methanol was collected. A vacuum was applied (1-2 mm-Hg) for ˜10 minutes during which all the Xylenes were distilled off. The solution was cooled under argon to about 140° C. and discharged in an aluminum tray where it was allowed to cool to room temperature to give 196.6 grams of product as an off-white solid (98% yield). The product was shown to be pure by 1H NMR spectroscopy with trace amounts of the mono-ester. Physical properties of this compound are shown in Table 2.

Aufarbeitung

  1. customTo a 3 neck 500 mL round bottomed flask equipped with a Dean Stark trap and condenser, thermocouple and argon inlet
  2. temperatureThe temperature was raised to 180° C
  3. customwas collected
  4. customfor ˜10 minutes
  5. distillationwere distilled off
  6. temperatureThe solution was cooled under argon to about 140° C.
  7. temperatureto cool to room temperature

Quellen und Nachweise

ORD-Eintrag
ord-40683622b8b04e32be95adc9124d2026
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741043B2

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