2,4-Dihydroxybenzoic Acid → HCID 21705210, compound

HRID 1938127Notes

Reaction equation

HRID 1938127 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][C:13]([C:15](Cl)=[O:16])=[CH2:14]>[OH-].[Na+].ClCCl>[C:15]([O:11][C:9]1[CH:10]=[C:2]([OH:1])[C:3](=[CH:7][CH:8]=1)[C:4]([OH:6])=[O:5])(=[O:16])[C:13]([CH3:14])=[CH2:12]

Participants

5

Reactant 2

HCID 14912,4-Dihydroxybenzoic AcidHCID 13528Methacryloyl chloride

Product 1

HCID 21705210HCID 21705210, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

2,4-dihydroxybenzoic acid (64.88 millimole, 10.0 g) was dissolved in an aqueous solution (300 g) of sodium hydroxide (1.7% by weight) to give an orange solution and the solution was cooled to 0° C. by ice bath. While stirring under a flow of nitrogen gas, a solution of methacryl chloride (8.0 g) in dichoromethane (100 ml) was added to the solution over a period of 60 minutes, and the solution was kept stirred at 0° C. for four hours after completing the addition. After the solution was stood to slowly warm to room temperature, the solution was further stirred overnight. The aqueous layer was separated from the organic layer, and to the aqueous layer was added an aqueous solution of 1N HCl so as to adjust its pH to 1. The solution was stood overnight to give colorless powder, and the powder was filtrated. The powder was washed by cold acidic water (100 ml) three times. After drying the powder under a reduced pressure at room temperature, the powder was recrystallized at 60° C. by an aqueous solution of methanol containing a small amount of hydroquinone to give colorless crystal having a needle shape: yield 10.11 g, 70.1%.

Workup

  1. customto give an orange solution
  2. stirringthe solution was kept stirred at 0° C. for four hours
  3. additionthe addition
  4. temperatureto slowly warm to room temperature
  5. customThe aqueous layer was separated from the organic layer
  6. additionto the aqueous layer was added an aqueous solution of 1N HCl so as
  7. waitThe solution was stood overnight
  8. customto give colorless powder
  9. filtrationthe powder was filtrated
  10. washThe powder was washed by cold acidic water (100 ml) three times
  11. customAfter drying the powder under a reduced pressure at room temperature
  12. customthe powder was recrystallized at 60° C. by an aqueous solution of methanol containing a small amount of hydroquinone
  13. customto give colorless crystal

Sources & evidence

ORD record
ord-2e88b5987c4d46718dd4071aee6916cc
Source dataset
uspto-grants-1997_12
Patent number
US05693320

Reaction notes

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