Water → 4-[4-(Methacryloyloxy)butoxy]benzenecarboxylic acid

HRID 1019329

Reaction equation

HRID 1019329 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1.[C:16](O)(=[O:20])[C:17]([CH3:19])=[CH2:18].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>ClC(Cl)(Cl)C.C(C1CC(=CN(C)C)C=C(C(C)(C)C)C=1O)(C)(C)C>[C:16]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1)(=[O:20])[C:17]([CH3:19])=[CH2:18]

Participants

7

Reactant 4

HCID 962WaterHCID 4093Methacrylic AcidHCID 6101p-Toluenesulfonic acidHCID 152185964-(4-Hydroxybutoxy)benzoic acid

Product 1

HCID 37201354-[4-(Methacryloyloxy)butoxy]benzenecarboxylic acidYield 60%

Reagents, catalysts & solvents 2

HCID 867583672,6 Di-tert-butyl-4-(dimethylaminomethylene)phenolCatalystHCID 62781,1,1-TrichloroethaneSolvent

Procedure

A solution of 282 g of 4-(4′-hydroxybutoxy)benzoic acid (1.34 mol), 325 ml of freshly distilled methacrylic acid (3.35 mol), 0.3 g of 2,6 di-tert-butyl-4-(dimethylaminomethylene)phenol (Ethanox® 703) and 23.7 g of p-toluenesulfonic acid in 1.1 l of 1,1,1-trichloroethane was refluxed for 10 hours on a water separator. The reaction mixture was cooled to 60° C.-70° C. and stirred into 2.51 of petroleum ether, and the precipitate was filtered off. After washing with petroleum ether, the precipitate was dried under reduced pressure at room temperature for 24 hours, giving 223.7 g of 4-(4′-methacryloxybutoxy)benzoic acid (yield 60%).

Workup

  1. temperatureThe reaction mixture was cooled to 60° C.-70° C.
  2. filtrationthe precipitate was filtered off
  3. washAfter washing with petroleum ether
  4. customthe precipitate was dried under reduced pressure at room temperature for 24 hours

Sources & evidence

ORD record
ord-19ed3d7c5f8940d19128299bfcfcf4cd
Source dataset
uspto-grants-2002_11
Patent number
US06486338B1

Linked notes

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