Methyl iodide → Bis(4-methylphenyl) methylphosphonate

HRID 354737Notes

Reaction equation

HRID 354737 reaction equation
[CH3:1]OP(C)(=O)OC.[P:8]([O:25]C1C=CC(C)=CC=1)([O:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)[O:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1.CI>>[C:10]1([O:9][P:8]([CH3:1])(=[O:25])[O:17][C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 12106Phosphorous acid, tris(methylphenyl) esterHCID 12958Dimethyl methylphosphonate

Product 1

HCID 185968Bis(4-methylphenyl) methylphosphonateYield 263.8%

Conditions

Temperature
245 °C

Procedure

A mixture of 64 g of methane phosphonic acid dimethyl ester (0.516 mol), 352 g of tris-p-cresyl phosphite (1.00 mol) and 2 ml of methyl iodide is slowly heated to 245° C. and tempered at this temperature for 30 minutes. Vacuum distillation yields 376 g of methane phosphonic acid di-p-cresyl ester (Bp1 mm 144° C.), 98.6% pure.

Workup

  1. distillationVacuum distillation

Sources & evidence

ORD record
ord-42d6038160d7478a90f32a234e0805a4
Source dataset
uspto-grants-1983_03
Patent number
US04377537

Reaction notes

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