Triphenylphosphine → HCID 18522737, compound

HRID 1065742Notes

Reaction equation

[C:1](=[O:12])([O:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])N.[CH2:13]([OH:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[C:1](=[O:12])([O:21][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[O:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10]

Participants

Conditions

Temperature: 270 °C

Procedure

30.94 g of isooctyl carbamate, 48.90 g of isooctanol, 0.40 g of triphenylphosphine and 2.0 ml of a 20% strength solution of diisobutyl-aluminium hydride in toluene were warmed together, whilst stirring. The mixture started to boil at about 165° C. The mixture was now heated in such a way that a continuous reflux of isooctanol was set up in a Vigreux column (jacket length 30 cm) fitted on the reaction vessel. The temperature was raised continuously to 270° C. over a period of 7 hours; after that time 2.78 g (91.3% of theory) of NH3 had been separated off and 24.95 g of liquid and a little solid had been distilled off (isooctanol, urethane and urea). The mixture was then subjected to fractional distillation. A fraction of 4.35 g with a boiling point14 of 81.5 (isooctanol) and a fraction of 46.96 g with a boiling point~ 0.05 of 98-102 (diisooctyl carbonate) resulted. Yield 92.33%, based on urethane employed.

Workup

customto boil at about 165° C
temperatureThe mixture was now heated in such a way that
customfitted on the reaction vessel
customafter that time 2.78 g (91.3% of theory) of NH3 had been separated off
distillation24.95 g of liquid and a little solid had been distilled off (isooctanol, urethane and urea)
distillationThe mixture was then subjected to fractional distillation

Sources & evidence

ORD record: ord-3595bd2090684439a673ba2665a03ed2
Source dataset: uspto-grants-1982_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04331610

Reaction notes

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