Ammonia → Propyl diphenylphosphinite

HRID 1421655Notes

Reaction equation

HRID 1421655 reaction equation
[CH2:1]([OH:4])[CH2:2][CH3:3].Cl[P:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.N>>[C:13]1([P:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[O:4][CH2:1][CH2:2][CH3:3])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 10311-PropanolHCID 66180Chlorodiphenylphosphine

Product 1

HCID 12633007Propyl diphenylphosphiniteYield 63%

Procedure

915 g (15.25 mol) of n-propanol are cooled to -15° C. with stirring under a nitrogen atmosphere. 330 g (1.5 mol) of chloro(diphenyl)phosphine are then added dropwise at this temperature with vigorous stirring in one hour and 15 minutes. 38 g (2.24 mol) of ammonia gas are then introduced at this temperature with further vigorous stirring. The mixture is then stirred for a further ten hours without cooling. After filtering off the ammonium chloride by suction, the filtrate is freed from propanol and excess ammonia in vacuo. The remaining residue is distilled (boiling point 122° C. at 0.4 mbar). 230 g of propyl diphenylphosphinite are obtained. This corresponds to a yield of 63% of theory.

Workup

  1. stirringwith vigorous stirring in one hour and 15 minutes
  2. stirringThe mixture is then stirred for a further ten hours
  3. temperaturewithout cooling
  4. filtrationAfter filtering off the ammonium chloride by suction
  5. distillationThe remaining residue is distilled (boiling point 122° C. at 0.4 mbar)

Sources & evidence

ORD record
ord-98ab22649c024b338047d8383fa98185
Source dataset
uspto-grants-2000_06
Patent number
US06077968

Reaction notes

Loading…