Hexane → HCID 22169093, compound

HRID 2229808Notes

Reaction equation

HRID 2229808 reaction equation
C[O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([CH3:11])[C:5]=1[OH:12].[Cl:14]OC(C)(C)C.CCCCCC>C(OCC)(=O)C>[Cl:14][C:8]1[C:7]([OH:10])=[C:6]([CH3:11])[C:5]([OH:12])=[C:4]([CH:9]=1)[C:3]([OH:2])=[O:13]

Participants

5

Reactant 3

HCID 8058HexaneHCID 118521Benzoic acid, 2,4-dihydroxy-3-methyl-, methyl esterHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 22169093HCID 22169093, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,4-dihydroxy-3-methylbenzoic acid methyl ester (9.9 g) in ethyl acetate (100 ml) was added tert-butyl hypochlorite (12.3 ml) under ice-cooling. After stirring for 2 hours, hexane (200 ml) was added, and the mixture was cooled with ice to allow precipitation of crystals. The crystals were collected by filtration, and dissolved in a mixed solvent of methanol (20 ml) and tetrahydrofuran (THF, 20 ml). A 1 M lithium hydroxide solution (40 ml) was added to the solution, and the mixture was refluxed under heating for 18 hours. The reaction mixture was concentrated, and a 10% aqueous citric acid solution was added to the residue, which was followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure to give the title compound (4.14 g, yield 37%).

Workup

  1. temperaturecooling
  2. temperaturethe mixture was cooled with ice
  3. customprecipitation of crystals
  4. filtrationThe crystals were collected by filtration
  5. dissolutiondissolved in a mixed solvent of methanol (20 ml) and tetrahydrofuran (THF, 20 ml)
  6. additionA 1 M lithium hydroxide solution (40 ml) was added to the solution
  7. temperaturethe mixture was refluxed
  8. temperatureunder heating for 18 hours
  9. concentrationThe reaction mixture was concentrated
  10. additiona 10% aqueous citric acid solution was added to the residue, which
  11. extractionwas followed by extraction with ethyl acetate
  12. washThe organic layer was washed with water and saturated brine
  13. dry with materialdried over anhydrous sodium sulfate
  14. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2b2e2590348f44fe8dfa670f5ef30b07
Source dataset
uspto-grants-2002_07
Patent number
US06420561B1

Reaction notes

Loading…