Hydroquinone → HCID 19426206, compound

HRID 742516Notes

Reaction equation

HRID 742516 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1.[C:23](O)(=[O:27])[C:24]([CH3:26])=[CH2:25].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C=CC(O)=CC=1)O>C(Cl)(Cl)Cl>[C:23]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:21][CH:22]=1)(=[O:27])[C:24]([CH3:26])=[CH2:25]

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 4093Methacrylic AcidHCID 6101p-Toluenesulfonic acidHCID 122971344-(11-hydroxyundecyloxy)benzoic acid

Product 1

HCID 19426206HCID 19426206, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 200 ml of chloroform were dissolved 15.0 g (48.6 mmol) of the compound (2), 60.0 g (697 mmol) of methacrylic acid, 2.0 g of p-toluenesulfonic acid, and 3.0 g of hydroquinone as polymerization inhibitor. The whole was refluxed for 13 hours under removing water formed. Then, after removal of solvent, the reaction mixture was poured into a plenty of ice-water, and the resulting precipitate was collected by filtration and dried after washing with water. The obtained white solid was recrystallized from acetone to obtain 14.5 g of p-(11-methacryloxyundecyloxy)benzoic acid (3) (yield: 78.9%).

Workup

  1. customas polymerization inhibitor
  2. temperatureThe whole was refluxed for 13 hours under removing water
  3. customformed
  4. customThen, after removal of solvent
  5. additionthe reaction mixture was poured into a plenty of ice-water
  6. filtrationthe resulting precipitate was collected by filtration
  7. customdried
  8. washafter washing with water
  9. customThe obtained white solid was recrystallized from acetone

Sources & evidence

ORD record
ord-f37d7496025b4ed3a2088773a36e2013
Source dataset
uspto-grants-1996_09
Patent number
US05554706

Reaction notes

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