1,2-Dichloroethane → Methyl 3-fluoro-4-hydroxybenzoate

HRID 1589723Notes

Reaction equation

HRID 1589723 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].Cl[CH2:13]CCl.CO.S(=O)(=O)(O)O>CCCCCC>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([O:7][CH3:13])=[O:6]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 887MethanolHCID 1118Sulfuric AcidHCID 1604563-Fluoro-4-hydroxybenzoic acid

Product 1

HCID 7019368Methyl 3-fluoro-4-hydroxybenzoateYield 91.6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

10.0 g (64.1 mM) of 3-fluoro-4-hydroxybenzoic acid, 150 ml of 1,2-dichloroethane, 80 ml of methanol and 10 ml of concentrated sulfuric acid were mixed, followed by refluxing for 5.5 hours under stirring and further stirring for 12 hours at room temperature. After the reaction, a solution of salt was added to the reaction mixture, followed by sufficient shaking to separate the reaction mixture. The organic layer was recovered from the reaction mixture and the water layer was subjected to extraction with methylene chloride to be added thereto. The resultant organic layer was washed with a 5%-aqueous solution of sodium hydrogencarbonate in a solution of salt and further washed with a solution of salt, followed by drying with anhydrous sodium sulfate. The sodium sulfate was recovered by filtration and the filtrate was condensed into a solid. Hexane was added to the solid and subjected to filtration to obtain 9.98 g of methyl 3-fluoro-4-hydroxybenzoate (Yield: 91.6%).

Workup

  1. temperatureby refluxing for 5.5 hours
  2. stirringfurther stirring for 12 hours at room temperature
  3. customAfter the reaction
  4. additiona solution of salt was added to the reaction mixture
  5. stirringby sufficient shaking
  6. customto separate the reaction mixture
  7. customThe organic layer was recovered from the reaction mixture
  8. extractionthe water layer was subjected to extraction with methylene chloride
  9. additionto be added
  10. washThe resultant organic layer was washed with a 5%-aqueous solution of sodium hydrogencarbonate in a solution of salt
  11. washfurther washed with a solution of salt
  12. dry with materialby drying with anhydrous sodium sulfate
  13. filtrationThe sodium sulfate was recovered by filtration
  14. customcondensed into a solid
  15. filtrationsubjected to filtration

Sources & evidence

ORD record
ord-cb8977e6c7564e278085be6777d30305
Source dataset
uspto-grants-1993_04
Patent number
US05200109

Reaction notes

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