Hydrochloric Acid → {1-[(2-Methylacryloyl)oxy]ethane-1,1-diyl}bis(phosphonic acid)

HRID 851233

Reaction equation

HRID 851233 reaction equation
[OH:1][C:2]([P:8]([OH:11])(=[O:10])[OH:9])([P:4]([OH:7])(=[O:6])[OH:5])[CH3:3].[C:12](Cl)(=[O:16])[C:13]([CH3:15])=[CH2:14].Cl>C(N(CC)CC)C>[C:12]([O:1][C:2]([P:4]([OH:7])(=[O:5])[OH:6])([P:8]([OH:11])(=[O:9])[OH:10])[CH3:3])(=[O:16])[C:13]([CH3:15])=[CH2:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3305Etidronic AcidHCID 13528Methacryloyl chloride

Product 1

HCID 22712909{1-[(2-Methylacryloyl)oxy]ethane-1,1-diyl}bis(phosphonic acid)Yield 65%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 5 g (0.024 mol) of 1-hydroxyethane-1,1-diphosphonic acid in 30 ml of triethylamine was gradually added 15.7 g (0.15 mol) of methacryloyl chloride with ice cooling. After the temperature was raised to room temperature, the mixture was stirred for ten hours. The reaction solution was acidified with aqueous hydrochloric acid and then extracted with diethyl ether. The resulting aqueous phase was alkalized with sodium hydroxide and then extracted again with diethyl ether. The resulting aqueous phase was chromatographed over Amberlite 120B (trade mark, Rohm & Haas Co.) and the solvent of the eluate was evaporated to give 4.3 g of a colorless oily substance which was identified to be 1-methacryloxyethane-1,1-diphosphonic acid (yield 65%).

Workup

  1. extractionextracted with diethyl ether
  2. extractionextracted again with diethyl ether
  3. customThe resulting aqueous phase was chromatographed over Amberlite 120B (trade mark, Rohm & Haas Co.)
  4. customthe solvent of the eluate was evaporated
  5. customto give 4.3 g of a colorless oily substance which

Sources & evidence

ORD record
ord-483cfbe87e224598bb1f0a3fe04d802d
Source dataset
uspto-grants-1983_05
Patent number
US04383052

Linked notes

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