(+-)-alpha-Pinene → Tetramethyl para-menthane-2,6-diyldiphosphonate

HRID 2052229

Reaktionsgleichung

Reaktionsgleichung von HRID 2052229
[P:1]([OH:6])([O:4][CH3:5])[O:2][CH3:3].C(O[O:12][C:13](C)(C)C)(C)(C)C.[CH3:17][C:18]1[CH:23]2[C:24]([CH3:26])([CH3:25])[CH:21]([CH2:22]2)[CH2:20][CH:19]=1>>[CH:18]1([CH3:17])[CH:19]([P:1](=[O:6])([O:4][CH3:5])[O:2][CH3:3])[CH2:20][CH:21]([CH:24]([CH3:26])[CH3:25])[CH2:22][CH:23]1[P:1](=[O:4])([O:12][CH3:13])[O:2][CH3:3]

Komponenten

4

Edukt 3

HCID 6654(+-)-alpha-PineneHCID 8033Di-tert-butyl peroxide2×HCID 94853Dimethyl ester phosphorous acid

Produkt 1

HCID 20377247Tetramethyl para-menthane-2,6-diyldiphosphonate

Versuchsvorschrift

In a manner similar to the previous examples, 233 ml of dimethyl hydrogen phosphite was stirred with 4.6 ml of di-tertiary-butyl peroxide at 140°-150° while α-pinene (81 ml) was added over a period of 15 minutes. After maintaining the reaction mixture at 140° for 18 hours, an additional 4.6 ml of di-tertiary-butyl peroxide was added. After heating an additional 30 minutes, the reaction mixture was subjected to distillation which provided the di-adduct. The NMR spectrum showed the methyl ester groups as a multiplet consisting mainly of 2 spikes at 3.70δ and 3.88δ along with the remainder of the protons between 0.7δ and 3.5δ.

Aufarbeitung

  1. additionwas added over a period of 15 minutes
  2. temperatureAfter maintaining the reaction mixture at 140° for 18 hours
  3. temperatureAfter heating an additional 30 minutes
  4. distillationthe reaction mixture was subjected to distillation which
  5. customprovided the di-adduct

Quellen und Nachweise

ORD-Eintrag
ord-b292ab66d59f4dcf9ec5687a35d2a024
Quelldatensatz
uspto-grants-1980_01
Patentnummer
US04183879

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