Hydroquinone → 4-(2-((2-Methyl-1-oxo-2-propen-1-yl)oxy)ethoxy)benzoic acid

HRID 847661Notes

Reaction equation

HRID 847661 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1.[C:14](O)(=[O:18])[C:15]([CH3:17])=[CH2:16].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C=CC(O)=CC=1)O>C(Cl)(Cl)Cl.O>[CH3:17][C:15](=[CH2:16])[C:14]([O:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)=[O:18]

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 4093Methacrylic AcidHCID 6101p-Toluenesulfonic acidHCID 43122544-(2-Hydroxyethoxy)benzenecarboxylic acid

Product 1

HCID 155900104-(2-((2-Methyl-1-oxo-2-propen-1-yl)oxy)ethoxy)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

50 g of p-(2-hydroxyethoxy)-benzoic acid, 130 g of methacrylic acid, 5 g of p-toluenesulfonic acid and 5 g of hydroquinone as an inhibitor are dissolved in 200 ml of CHCl3 and the solution is refluxed in a 500 ml flask, fitted with a water separator and reflux condenser, until about 6 ml of water have separated out (about 20 hours). The cooled solution is introduced into about 1 liter of ether and is washed with 5 portions of water each of about 200 ml. After drying the solution with Na2SO4, the solvents are stripped off and the crude product is recrystallized as described under 1.1.1.

Workup

  1. temperaturethe solution is refluxed in a 500 ml flask
  2. temperaturereflux condenser
  3. customuntil about 6 ml of water have separated out (about 20 hours)
  4. additionThe cooled solution is introduced into about 1 liter of ether
  5. washis washed with 5 portions of water each of about 200 ml
  6. dry with materialAfter drying the solution with Na2SO4
  7. customthe crude product is recrystallized

Sources & evidence

ORD record
ord-784145f219334698b7371b675a7be1e1
Source dataset
uspto-grants-1981_10
Patent number
US04293435

Reaction notes

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