Sulfuric Acid → HCID 58240635, compound

HRID 1802830Notes

Reaction equation

HRID 1802830 reaction equation
S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].[C:11]([O:14][C:15]1[CH:20]2[C:21]([CH3:27])([CH3:26])[CH:22]3[CH2:25][C:19]2([CH2:24][CH2:23]3)[C:18]([CH3:29])([CH3:28])[CH2:17][CH:16]=1)(=[O:13])[CH3:12]>C(OC(C)=C)(=O)C>[C:11]([O:14][C:15]1[CH2:16][CH2:17][C:18]([CH3:29])([CH3:28])[C:19]23[CH2:25][CH:22]([CH2:23][CH2:24]2)[C:21]([CH3:27])([CH3:26])[C:20]=13)(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 58240632HCID 58240632, compound

Product 1

HCID 58240635HCID 58240635, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 7916Isopropenyl acetateSolvent

Procedure

Concentrated sulphuric acid (0.7 ml) was added to a stirred solution of isolongifolan-8-one (1, 30.0 g, 90% pure, 0.12 mol) in isopropenyl acetate (150 ml). The reaction mixture was heated at reflux for 45 minutes, basified with saturated aqueous solution of sodium bicarbonate (200 ml) and extracted with MTBE (200 ml). The filtrate was washed with water (2×200 ml), dried (Na2SO4), concentrated in vacuo and distilled under reduced pressure to give (at 95° C./<1 mbar) a mixture of 2,2,7,7-tetramethyltricyclo[6.2.1.01.6]undec-4-en-5-yl acetate and 2,2,7,7-tetramethyltricyclo[6.2.1.01.6]undec-5-en-5-yl acetate (2a+2b: 70+25.5%, 30.5 g, 90% yield, pale yellow oil).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 45 minutes
  3. extractionextracted with MTBE (200 ml)
  4. washThe filtrate was washed with water (2×200 ml)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. distillationdistilled under reduced pressure
  8. customto give (at 95° C./<1 mbar)

Sources & evidence

ORD record
ord-201153d2ec5243f6aabaff8cf97007e0
Source dataset
uspto-grants-2013_01
Patent number
US08349890B2

Reaction notes

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