Hydrochloric Acid → HCID 54201759, compound

HRID 838828Notes

Reaction equation

HRID 838828 reaction equation
C[O-].[Na+].[CH3:4][O:5][P:6]([CH2:10][C:11]([O:13][CH3:14])=[O:12])(=[O:9])[O:7][CH3:8].[C:15]([O:23][CH3:24])(=[O:22])/[CH:16]=[CH:17]\[C:18]([O:20][CH3:21])=[O:19].Cl>CO>[CH3:4][O:5][P:6]([CH:10]([C:11]([O:13][CH3:14])=[O:12])[CH:16]([C:15]([O:23][CH3:24])=[O:22])[CH2:17][C:18]([O:20][CH3:21])=[O:19])(=[O:9])[O:7][CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 80029Trimethyl phosphonoacetateHCID 5271565Dimethyl maleateHCID 10942334Sodium Methoxide

Product 1

HCID 54201759HCID 54201759, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.09 mol of sodium methylate in 25 cc of methanol was added within 45 minutes to a mixture of 136.5 g (0.75 mol) of carbomethoxy-methane-phosphonic acid dimethyl ester and 108 g (0.75 mol) of dimethyl maleate. The temperature was found to increase from 22° C to 41° C. The whole was allowed to further react for 30 minutes at 100° C. After neutralization by the addition of 5 cc of concentrated hydrochloric acid and filtration, all volatile matter was distilled off under vacuum at a base temperature up to 120° C. 1,2,3-tricarbomethoxy-propane-1-phosphonic acid dimethyl ester was obtained in a crude yield of 237 g (97 % of the theoretical). The ester had a boiling point of 169°-172° C under 0.7 mm of mercury. n25D = 1.4520.

Workup

  1. temperatureto increase from 22° C to 41° C
  2. customto further react for 30 minutes at 100° C
  3. distillationall volatile matter was distilled off under vacuum at a base temperature up to 120° C

Sources & evidence

ORD record
ord-f3ec0c7e50444a11a4b53517b5f01d04
Source dataset
uspto-grants-1978_06
Patent number
US04093538

Reaction notes

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