Methacrylic Acid → HCID 22311647, compound

HRID 1604196Notes

Reaction equation

HRID 1604196 reaction equation
[C:1]([O:4][CH2:5][CH2:6][O:7][CH:8]=[CH2:9])(=[O:3])[CH3:2].[C:10](O)(=[O:14])[C:11](C)=C.N1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[C:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:14][CH:10]=[CH2:11])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 4093Methacrylic AcidHCID 161440Pyridine 4-methylbenzene-1-sulfonateHCID 10920540HCID 10920540, compound

Product 1

HCID 22311647HCID 22311647, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The thus obtained acetoxyethylvinylether by 19.5 grams (0.15 mols) and methacrylic acid by 15.5 grams (0.18 mols) were dissolved into methylene chloride. Then, 0.38 grams (0.0015 mols) of p-toluenesulfonic acid pyridine salt was added into the mixture, and stirred for complete dissolution. The resultant mixture is stood at room temperature for 6 hours. Then, the mixture was washed three times with 2.5% aqueous sodium hydroxide, and six times with water. Then, the resultant mixture was dehydrated with magnesium sulfate. After filtering magnesium sulfate out, solvent was removed by means of an evaporator. Then, the resultant residue was distilled under reduced pressure, thereby there was obtained 29.6 grams of acetoxyethoxyethylvinylether (b.p. 100-105° C./0.07 mmHg). The yield was 93%.

Workup

  1. washThen, the mixture was washed three times with 2.5% aqueous sodium hydroxide, and six times with water
  2. filtrationAfter filtering magnesium sulfate out
  3. customsolvent was removed by means of an evaporator
  4. distillationThen, the resultant residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-1b8646e423fb41c7be090a0838063de3
Source dataset
uspto-grants-1999_11
Patent number
US05994025

Reaction notes

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