Pyridine → Allyldiphenylphosphine oxide

HRID 1287965Notes

Reaction equation

HRID 1287965 reaction equation
[Cl-].[C:2]1([PH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([OH:18])C=C.N1C=C[CH:22]=[CH:21][CH:20]=1>CCOCC>[CH2:20]([P:8](=[O:18])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH:21]=[CH2:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7858Allyl AlcoholHCID 19695023Diphenylphosphane chloride

Product 1

HCID 138131Allyldiphenylphosphine oxide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
178 °C

Procedure

A mixture of diphenylphosphine chloride (11 g, 0.05 mol), allyl alcohol (2.9 g, 0.05 mol) in 50 ml of anhydrous ether is stirred at room temperature while slowly adding pyridine (4.0 g, 0.05 mol) to it. After 40 minutes, the pyridine hydrochloride is filtered off and the ether removed by distillation. The liquid residue is heated to 150°, whereupon an exothermic reactions sets in raising the temperature quickly to 178° C. The material is then distilled, b.p. 168°-175° C/0.4 mm, whereupon it crystallizes, m.p. 108° identical to the allyl diphenylphosphine oxide made by oxidation of the phosphine. Allyl diphenylphosphine oxide prepared by this method is reported; b.p. 200°-202° C/2 mm; m.p. 94°-96° C.

Workup

  1. filtrationthe pyridine hydrochloride is filtered off
  2. customthe ether removed by distillation
  3. temperatureThe liquid residue is heated to 150°, whereupon an exothermic reactions sets
  4. distillationThe material is then distilled
  5. customb.p. 168°-175° C/0.4 mm, whereupon it crystallizes
  6. customAllyl diphenylphosphine oxide prepared by this method

Sources & evidence

ORD record
ord-f3aa7453e6974c9383c00c53f3ada650
Source dataset
uspto-grants-1976_10
Patent number
US03987009

Reaction notes

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