HCID 86641270, compound → 2-Propenoic acid, 2-methyl-, 3-phosphonopropyl ester

HRID 386356Notes

Reaction equation

HRID 386356 reaction equation
[C:1]([O:6][CH2:7][CH2:8][CH2:9][P:10](=[O:21])([O:16][Si](C)(C)C)[O:11][Si](C)(C)C)(=[O:5])[C:2]([CH3:4])=[CH2:3]>CO>[C:1]([O:6][CH2:7][CH2:8][CH2:9][P:10](=[O:11])([OH:21])[OH:16])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

3

Reactant 1

HCID 86641270HCID 86641270, compound

Product 1

HCID 112757882-Propenoic acid, 2-methyl-, 3-phosphonopropyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Di(trimethylsilyl) 3-methacryloyloxypropylphosphonate (34.0 g; 0.096 moles) was dissolved in methanol (115 ml). The solution was stirred at room temperature for 2 hours. The solvent was vacuum distilled on a rotary evaporator to give 3-methacryloyloxypropyl phosphonic acid as a highly viscous, colorless oil (19.9 g; yield 99%). 1H NMR (DMSO-d6, δ ppm) 1.52-1.66 (m, 2H, CH2—P), 1.74-1.93 (m, 2H, CH2—CH2—P), 1.87 (s, 3H, CH3), 4.12 (t, 2H, CH2—O), 5.66 (s, 1H, CH═), 6.02 (s, 1H, CH═). 31P NMR (DMSO-d6, δ ppm) 27.06.

Workup

  1. distillationdistilled on a rotary evaporator

Sources & evidence

ORD record
ord-ec981899a5fe45459172a4c8beacbd9c
Source dataset
uspto-grants-2013_02
Patent number
US08372516B2

Reaction notes

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