Sulfuric Acid → HCID 19834510, compound

HRID 2051084Notes

Reaction equation

HRID 2051084 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].S(=O)(=O)(O)O.C(O[C:17](=O)[CH3:18])(=O)C.[F:20][C:21]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24].[CH2:33]1CCCCC1>>[C:17]12([C:28]3[C:29]([O:31][CH3:32])=[CH:30][C:21]([F:20])=[C:22]([CH:27]=3)[C:23]([O:25][CH3:26])=[O:24])[CH2:18][CH:2]3[CH2:1][CH:6]([CH2:5][CH:4]([CH2:3]3)[CH2:33]1)[CH2:7]2

Participants

6

Reactant 5

HCID 1118Sulfuric Acid2×HCID 7918Acetic AnhydrideHCID 8078CyclohexaneHCID 8900HeptaneHCID 21255685Methyl 2-fluoro-4-methoxybenzoate

Product 1

HCID 19834510HCID 19834510, compound

Procedure

In a 100 ml flask, in a nitrogen atmosphere, are placed 2.48 g of I-adamantanol and 10 ml of n-heptane. Then 0.034 ml concentrated sulfuric acid and 1.76 ml of acetic anhydride are added dropwise. After one hour of agitation, there are added 0.87 ml of concentrated sulfuric acid and then a suspension of 2 g of methyl 2-fluoro-4-methoxybenzoate in 10 ml of cyclohexane. After 16 hours of reaction at room temperature, agitation is stopped and one separates the upper layer. The solvents heptane and cyclohexane are evaporated and then the product is extracted with dichloromethane. The organic phase is washed with aqueous bicarbonate solution, dried over magnesium sulfate and filtered on a Buchner funnel. After evaporation of the solvent under reduced pressure at 40° C., the product is dissolved in a 50:50 mixture of dichloromethane and hexane and then purified by filtration using a silica column. After passage of a liter of 50:50 dichloromethane/hexane eluent, one evaporates the solvents under reduced pressure at 30° C. and then dries the product in an oven at 50° C. for 24 hours. Thus were obtained 3 g of the pure product melting at 82°-88° C.

Workup

  1. customIn a 100 ml flask, in a nitrogen atmosphere, are placed
  2. customAfter 16 hours of reaction at room temperature
  3. customThe solvents heptane and cyclohexane are evaporated
  4. extractionthe product is extracted with dichloromethane
  5. washThe organic phase is washed with aqueous bicarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered on a Buchner funnel
  8. customAfter evaporation of the solvent under reduced pressure at 40° C.
  9. dissolutionthe product is dissolved in a 50:50 mixture of dichloromethane and hexane
  10. filtrationpurified by filtration
  11. customAfter passage of a liter of 50:50 dichloromethane/hexane eluent, one evaporates the solvents under reduced pressure at 30° C.
  12. customat 50° C.
  13. customfor 24 hours

Sources & evidence

ORD record
ord-f4b417ace4b9449a9129be2238ea71ae
Source dataset
uspto-grants-1991_05
Patent number
US05015758

Reaction notes

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