Sulfuric Acid → HCID 13978314, compound

HRID 2260104Notes

Reaction equation

HRID 2260104 reaction equation
[CH3:1][C:2](=[CH2:4])[CH3:3].[CH:5]1([C:10]([OH:12])=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6]1.OS(O)(=O)=O>C(O)(C)(C)C>[CH:5]1([C:10]([O:12][C:2]([CH3:4])([CH3:3])[CH3:1])=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 18840Cyclopentanecarboxylic acid

Product 1

HCID 13978314HCID 13978314, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Cool a metal bomb in a CO2 -acetone bath and charge with isobutylene (150 ml), cyclopentanecarboxylic acid (29.4 g, 0.26 mol), t-butanol (4 ml) and H2SO4 (1 ml). Remove the bomb from the cold-bath, seal and stir for 3 days. Cool the bomb in a CO2 -acetone bath, open to the atmosphere and evaporate isobutylene under a stream of N2 while allowing the reaction mixture to attain R.T. Add Et2O (300 ml) and wash the mixture with sat'd NaHCO3 (300 ml) and sat'd NaCl, then dry (MgSO4), filter and concentrate to obtain a colorless oil (41.5 g, 95%) which is used without further purification. 1H Nmr (CDCl3) δ2.58 (1H, m), 1.90-1.35 (8H, m), 1.39 (9H, s).

Workup

  1. temperatureCool a metal bomb in a CO2 -acetone bath
  2. customRemove the bomb from the cold-bath
  3. customseal
  4. temperatureCool the bomb in a CO2 -acetone bath
  5. customopen to the atmosphere and evaporate isobutylene under a stream of N2
  6. customto attain R.T
  7. washAdd Et2O (300 ml) and wash the mixture with sat'd NaHCO3 (300 ml)
  8. dry with materialdry (MgSO4)
  9. filtrationfilter
  10. concentrationconcentrate

Sources & evidence

ORD record
ord-833792508c6e4c1a9f771fef42892ab6
Source dataset
uspto-grants-1995_12
Patent number
US05476847

Reaction notes

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