Ethyl Acetate → Triphenylphosphine Oxide

HRID 1981074Notes

Reaction equation

HRID 1981074 reaction equation
[C:1]1([P:7](=S)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OCC)(=[O:23])C>>[C:1]1([P:7](=[O:23])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 19758Phosphine sulfide, triphenyl-

Product 1

HCID 13097Triphenylphosphine Oxide

Procedure

Through a mixture of triphenylphosphine sulfide (11.03 g) and ethyl acetate (200 ml) is bubbled chlorine gas (ca. 2.2 molar equivalents) at room temperature. The resulting mixture is neutralized with aqueous 6% sodium hydrogen carbonate (350 ml) and stirred at room temperature for 10 minutes. The reaction mixture is then worked up as in the case of Example 1 to give triphenylphosphine oxide (10 g). m.p. 154°-157° C.

Workup

  1. customis bubbled chlorine gas (ca. 2.2 molar equivalents) at room temperature

Sources & evidence

ORD record
ord-384d3468add5457d8f0823c6c51512ec
Source dataset
uspto-grants-1985_04
Patent number
US04511738

Reaction notes

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