Benzene → HCID 19096630, compound

HRID 486852Notes

Reaction equation

HRID 486852 reaction equation
[Cl:1][CH2:2][CH:3]1[O:8][C:7](=[O:9])[CH2:6][CH:5](O)[CH2:4]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>C(OCC)(=O)C>[Cl:1][CH2:2][C:3]1[O:8][C:7](=[O:9])[CH2:6][CH2:5][CH:4]=1

Participants

5

Reactant 3

HCID 241Benzene2×HCID 6101p-Toluenesulfonic acidHCID 22556038HCID 22556038, compound

Product 1

HCID 19096630HCID 19096630, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 50 mg (0.304 mmol) of (+)-6-chloromethyl-4-hydroxytetrahydropyran-2-one obtained in Example 3, 57.8 mg (0.304 mmol) of p-toluenesulfonic acid and 5 ml of benzene was refluxed for 30 minutes. After completion of the reaction, benzene was distilled off and distilled water were added thereto, and the solution was extracted with dichloromethane, followed by drying over anhydrous magnesium sulfate. After the solvent was distilled off, the resultant residue was subjected to column chromatography (an eluent of hexane:ethyl acetate=4:1), thereby obtaining 35.8 mg (yield 81%) of (-)-6- chloromethyldihydropyran-2-one.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. distillationwas distilled off
  3. distillationdistilled water
  4. additionwere added
  5. extractionthe solution was extracted with dichloromethane
  6. dry with materialby drying over anhydrous magnesium sulfate
  7. distillationAfter the solvent was distilled off

Sources & evidence

ORD record
ord-d9bf080b1ce74292a2a26552e14be1bd
Source dataset
uspto-grants-1994_03
Patent number
US05292891

Reaction notes

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