Sulfuric Acid → HCID 13651711, compound

HRID 1701184Notes

Reaction equation

HRID 1701184 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.COC1C=CC(O)=CC=1.[OH:27][CH2:28][C:29]([CH3:33])([CH3:32])[CH:30]=O.S(=O)(=O)(O)O>C(Cl)(Cl)Cl.[Cu].O>[C:1]([O:6][CH2:30][C:29]([CH3:33])([CH3:32])[CH:28]=[O:27])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

9

Reactant 5

HCID 1118Sulfuric AcidHCID 4093Methacrylic AcidHCID 6101p-Toluenesulfonic acidHCID 90154-MethoxyphenolHCID 116993-Hydroxy-2,2-dimethylpropionaldehyde

Product 1

HCID 13651711HCID 13651711, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

320 parts of methacrylic acid, 4 parts of p-toluene-sulfonic acid, 1 parts of copper-II chloride and 1.6 parts of hydroquinone monomethyl ether are dissolved in 1,200 parts of chloroform in a reaction vessel equipped with a reflux condenser and stirrer, and the solution is heated to the boil. A solution of 344 parts of hydroxypivalaldehyde in 1,200 parts of chloroform is run into the boiling solution over 4 hours. After this addition, 4 parts of 96% strength sulfuric acid are added and the water formed during the reaction is distilled off azeotropically. After completion of the reaction, and after cooling, the reaction mixture is washed with dilute aqueous sodium bicarbonate solution. After distilling off the chloroform under reduced pressure until the boiling point reaches 45° C., the residue is distilled in a thin film evaporator at 95° C./0.4 mm Hg. 274 parts of methacryloxypivalaldehyde (48% of theory, based on hydroxyaldehyde) of boiling point 51°-56° C./0.3 mm Hg are obtained. Analyses:

Workup

  1. customequipped with a reflux condenser and stirrer
  2. temperaturethe solution is heated to the boil
  3. additionare added
  4. distillationis distilled off azeotropically
  5. customAfter completion of the reaction
  6. temperatureafter cooling
  7. washthe reaction mixture is washed with dilute aqueous sodium bicarbonate solution
  8. distillationAfter distilling off the chloroform under reduced pressure until the boiling point
  9. customreaches 45° C.
  10. distillationthe residue is distilled in a thin film evaporator at 95° C./0.4 mm Hg

Sources & evidence

ORD record
ord-682aaf85657b4b6e882eb9f1963c1639
Source dataset
uspto-grants-1980_03
Patent number
US04191838

Reaction notes

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