Methanesulfonic Acid → HCID 23293363, compound

HRID 375778Notes

Reaction equation

HRID 375778 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7](O)=[CH:8][CH:9]=1)=[O:3].CS(O)(=O)=[O:13].[O:16]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17]1>C(OCC)(=O)C>[O:16]1[CH2:17][CH2:18][CH:19]([O:13][CH2:1][C:2]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[O:3])[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 74694'-HydroxyacetophenoneHCID 80803,4-dihydro-2H-pyran

Product 1

HCID 23293363HCID 23293363, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Hydroxyacetophenone (75.00 g, 0.55 mol) was dissolved in ethyl acetate (300 ml) and a catalytic amount of methanesulfonic acid. The solution was cooled to 0°-4° C. Dihydropyran (204 ml, 2.20 moles, 4.0 eq) was slowly added. At the end of the addition, the ice-water bath was removed and the reaction was allowed to proceed at room temperature. A few minutes later a heavy white precipitate was formed and the slurry was transferred into a separatory funnel where it was washed with water. The organic layer was dried over anhydrous sodium sulfate. Removal of the solvent under reduced pressure afforded a white fluffy solid. The solid was recrystallized from hexane. The yield was quantitative.

Workup

  1. temperatureThe solution was cooled to 0°-4° C
  2. additionAt the end of the addition
  3. customthe ice-water bath was removed
  4. customto proceed at room temperature
  5. customA few minutes later a heavy white precipitate was formed
  6. customthe slurry was transferred into a separatory funnel
  7. washwhere it was washed with water
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. customRemoval of the solvent under reduced pressure
  10. customafforded a white fluffy solid
  11. customThe solid was recrystallized from hexane

Sources & evidence

ORD record
ord-0109a8fb328342279e0743ffd463bcdd
Source dataset
uspto-grants-1996_01
Patent number
US05487885

Reaction notes

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