Hydrochloric Acid → Bis[2-(acryloyloxy)ethyl] benzene-1,3-dicarboxylate

HRID 2173896Notes

Reaction equation

HRID 2173896 reaction equation
[C:1]([O:5][CH2:6][CH2:7][OH:8])(=[O:4])[CH:2]=[CH2:3].C(C1C=C(C)C=[C:15]([C:20](C)(C)C)[C:14]=1[OH:24])(C)(C)C.[C:25](Cl)(=[O:35])[C:26]1[CH:34]=[CH:33][CH:32]=[C:28]([C:29](Cl)=[O:30])[CH:27]=1.Cl>N1C=CC=CC=1.C1(C)C=CC=CC=1>[C:1]([O:5][CH2:6][CH2:7][O:8][C:25](=[O:35])[C:26]1[CH:34]=[CH:33][CH:32]=[C:28]([C:29]([O:5][CH2:6][CH2:7][O:8][C:14](=[O:24])[CH:15]=[CH2:20])=[O:30])[CH:27]=1)(=[O:4])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7451Isophthaloyl chlorideHCID 131652-Hydroxyethyl acrylate2×HCID 314042,6-Di-tert-butyl-4-methylphenol

Product 1

HCID 57107493Bis[2-(acryloyloxy)ethyl] benzene-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 22007288Pyridine tolueneSolvent

Procedure

A 500 ml round-bottom flask was initially charged with 64.1 g of hydroxyethyl acrylate in 100 ml of pyridine/toluene (1:1, v/v) together with 0.1 g of 2,6-di-tert-butyl-4-methylphenol at 0° C., and 56.1 g of isophthaloyl chloride were slowly added dropwise. The mixture was stirred at room temperature until the hydroxyethyl acrylate content had fallen below 0.1%. Thereafter, the mixture was poured onto 0.5 l of ice-water and acidified with 1 N aqueous hydrochloric acid. The aqueous phase was extracted three times with 0.5 l each time of tert-butyl methyl ether. The organic phase was washed with 10% sodium hydrogencarbonate solution, dried over sodium sulfate and filtered. Another 0.1 g of 2,6-di-tert-butyl-4-methylphenol was added and the organic solvent was distilled off. The product was obtained as a colorless oil.

Workup

  1. extractionThe aqueous phase was extracted three times with 0.5 l each time of tert-butyl methyl ether
  2. washThe organic phase was washed with 10% sodium hydrogencarbonate solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. additionAnother 0.1 g of 2,6-di-tert-butyl-4-methylphenol was added
  6. distillationthe organic solvent was distilled off
  7. customThe product was obtained as a colorless oil

Sources & evidence

ORD record
ord-8fb1806cc70d4ea5a3c34c0a96fc0b64
Source dataset
uspto-grants-2015_06
Patent number
US09057950B2

Reaction notes

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