Hydroquinone → 4-Hydroxybutyl acrylate

HRID 1824651Notes

Reaction equation

HRID 1824651 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].[C:7](O)(=[O:10])[CH:8]=[CH2:9].S(=O)(=O)(O)O.C1(C=CC(O)=CC=1)O.C1(C)C=CC=CC=1>>[C:7]([O:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:6])(=[O:10])[CH:8]=[CH2:9]

Participants

6

Reactant 5

HCID 785HydroquinoneHCID 1118Sulfuric AcidHCID 1140TolueneHCID 6581Acrylic AcidHCID 80641,4-Butanediol

Product 1

HCID 755884-Hydroxybutyl acrylate

Procedure

Two mols of 1,4-butanediol, 2 mols of acrylic acid, 0.1 ml of sulfuric acid and 0.001 mol of hydroquinone were dissolved in 100 mol of toluene, and the solution was refluxed for 4 hours while removing water generated. After the completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was purified through silica gel column chromatography using acetone as an eluent to obtain 4-hydroxybutyl acrylate. One mol of 4-hydroxybutyl acrylate obtained, 1 mol of catechol and 1 mol of borane were reacted in dichloromethane at room temperature, and 1 mol of LiBr was further added and dissolved to obtain a desired compound.

Workup

  1. temperaturethe solution was refluxed for 4 hours
  2. customwhile removing water
  3. customAfter the completion of the reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-a70d019591a54dacaed9e363d9b45f9a
Source dataset
uspto-grants-2006_05
Patent number
US07045242B2

Reaction notes

Loading…