Phenyl phosphorus dichloride → Naphthalene

HRID 1076076Notes

Reaction equation

HRID 1076076 reaction equation
[Cl-].[Cl-].[C:3]1(P)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:10]1(P(Cl)Cl)[CH:15]=CC=[CH:12][CH:11]=1.[P:19]([Cl:22])([Cl:21])[Cl:20].[Cl-].[Cl-].C1(C)C=CC(P)=CC=1.[O:33]=[P:34]([Cl:37])([Cl:36])[Cl:35]>C1(C)C=CC=CC=1.C1C=CC=CC=1>[O:33]=[P:34]([Cl:37])([Cl:36])[Cl:35].[CH:7]1[C:8]2[C:3](=[CH:15][CH:10]=[CH:11][CH:12]=2)[CH:4]=[CH:5][CH:6]=1.[P:19]([Cl:22])([Cl:21])[Cl:20]

Participants

10

Reactant 5

HCID 12573Phenyl phosphorus dichlorideHCID 24387Phosphorus trichloride2×HCID 24813Phosphorus oxychlorideHCID 20975587HCID 20975587, compoundHCID 21541738HCID 21541738, compound

Product 3

HCID 931NaphthaleneHCID 24387Phosphorus trichlorideHCID 24813Phosphorus oxychloride

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1140TolueneSolvent

Procedure

Phenylphosphine dichloride, C6H5PCl2, was the only product detected when benzene and PCl3 were fed to the catalytic reactor. A mixture of o, m, and p-tolylphosphine dichloride, CH3C6H4PCl2, was the only organic product detected when toluene and PCl3 were used as the starting material. A small amount, < 1%, of POCl3 was observed. A mixture of α- and β-naphthylphosphine dichloride, C10H7PCl2, was produced, along with a small amount of POCl3 when naphthalene and PCl3 were used as the feed. A small amount of 2,5, dimethyl phenylphosphine dichloride was detected when p-xylene and PCl3 were used as the feed. Traces of toluene, POCl3 and an unidentified product were observed with the latter. The results are summarized in more detail in Table VI.

Sources & evidence

ORD record
ord-cb103383c05b46dca18ef6eab71a0b57
Source dataset
uspto-grants-1976_05
Patent number
US03954859

Reaction notes

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