Methyl Acrylate → Methyl 3‐[methoxy(methyl)phosphoryl]propanoate

HRID 374239Notes

Reaction equation

HRID 374239 reaction equation
[CH3:1][P:2]([O:6][CH3:7])(=[O:5])OC.[C:8]([O:12][CH3:13])(=[O:11])[CH:9]=[CH2:10].COC>CO>[CH3:7][O:6][P:2]([CH3:1])([CH2:10][CH2:9][C:8]([O:12][CH3:13])=[O:11])=[O:5]

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 8254Dimethyl EtherHCID 12958Dimethyl methylphosphonate

Product 1

HCID 14848975Methyl 3‐[methoxy(methyl)phosphoryl]propanoateYield 97.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

80 g of methanol are mixed at room temperature under nitrogen with 216 g of dimethyl methanephosphonate and the mixture is treated dropwise at room temperature with 172 g of methyl acrylate, the temperature rising to 70° C. At the end of the dropwise addition the mixture is further stirred for 1 hour, at the end of which period about 90 g of dimethyl ether have separated in a fitted cooling trap. Excess methanol used as solvent is then removed by vacuum distillation. The crude product is obtained in a yield of 365 g with a 96.4% purity, which represents a theoretical yield of 97.7%. The boiling point of a distilled sample is 96° C. at 0.027 mbar. The 1H-NMR spectrum and the CHP analysis of the product correspond to those of a comparison sample, synthesized by an independent route.

Workup

  1. customrising to 70° C
  2. additionAt the end of the dropwise addition the mixture
  3. customhave separated in a fitted
  4. temperaturecooling trap
  5. customis then removed by vacuum distillation

Sources & evidence

ORD record
ord-31e7919ab5fb4c6788cfbe684166c6b1
Source dataset
uspto-grants-1992_11
Patent number
US05166385

Reaction notes

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