Lactic Acid → 4,4'-Methylenebis (alpha-hydroxypropiamidocyclohexane)

HRID 371175

Reaktionsgleichung

Reaktionsgleichung von HRID 371175
[CH2:1]([CH:9]1[CH2:14][CH2:13][CH:12]([NH2:15])[CH2:11][CH2:10]1)[CH:2]1[CH2:7][CH2:6][CH:5]([NH2:8])[CH2:4][CH2:3]1.[C:16]([OH:21])(=O)[CH:17]([CH3:19])[OH:18]>O>[CH2:1]([CH:2]1[CH2:3][CH2:4][CH:5]([NH:8][C:16](=[O:21])[CH:17]([OH:18])[CH3:19])[CH2:6][CH2:7]1)[CH:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16](=[O:21])[CH:17]([OH:18])[CH3:19])[CH2:11][CH2:10]1

Komponenten

4

Edukt 2

HCID 612Lactic AcidHCID 156604,4'-Diaminodicyclohexylmethane

Produkt 1

HCID 537552054,4'-Methylenebis (alpha-hydroxypropiamidocyclohexane)

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Molten 4,4'-methylenebis(cyclohexylamine) (224.0 g, 1.065 moles) was placed in a 1 liter round bottom flask and 85% lactic acid (225.5 g, 2.13 moles) added slowly through an addition funnel with stirring and cooling. The resultant liquid was then heated in an oil bath to 190° C. whereupon distillation of water occurred. Heating was continued at 190° C. for 4 hours after which time distillation of water subsided and the liquid was poured into a Pyrex baking dish. Upon cooling the product solidified into a clear, amber colored glass. The solid was broken up and recrystallized twice from tetrahydrofuran containing 10% methanol to give lustrous, white flakes; m.p. 195°-199° C.; infrared (Nujol), 1640 cm-1, 3300 cm-1 ; proton nuclear magnetic resonance (DMSO-d6 /TMS, 100 MHz), δ0.6-1.5 (complex multiplet with doublet superimposed at δ1.15, 18 protons), δ1.5-1.8 (doublet, 8 protons), δ3.50 (broad singlet, 2 protons), δ3.7-4.1 (multiplet, 2 protons), δ5.35 (doublet, 2 protons), δ7.30 (doublet, 2 protons).

Aufarbeitung

  1. temperaturecooling
  2. temperatureHeating
  3. distillationafter which time distillation of water
  4. additionthe liquid was poured into a Pyrex baking dish
  5. temperatureUpon cooling the product
  6. customrecrystallized twice from tetrahydrofuran containing 10% methanol
  7. customto give lustrous

Quellen und Nachweise

ORD-Eintrag
ord-44822b4a34c644528dea7abd1e473fbc
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04529792

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