Sulfuric Acid → Hexahydro-2H-3,5-methanocyclopenta[b]furan-2-one
Reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[C:8]([OH:10])=[O:9].S(=O)(=O)(O)O>>[CH:2]12[CH:1]3[CH2:7][CH:4]([CH2:5][CH:6]3[O:9][C:8]1=[O:10])[CH2:3]2Participants
Procedure
The carboxylic acid (51 g) prepared in Example 1 was slowly added with stirring to sulfuric acid (500 ml, 75 percent by volume). The exothermic reaction that ensued was controlled by an ice-water bath. The reaction subsided after several minutes and the resulting dark solution was then kept at room temperature for about 10 days. The solution was then poured into ice-water (150 ml) and the product then extracted with diethyl ether (three 200-ml portions). The combined extracts were washed with saturated sodium bicarbonate solution (200 ml). The ether was evaporated yielding 45.5 g of 6-oxatricyclo[3.2.1.13,8 ]nonan-7-one which was about 91 percent of theory. The product was identified by GC-mass spectrometric, infrared and melting point analysis.
Workup
- customThe exothermic reaction
- customthat ensued was controlled by an ice-water bath
- waitThe reaction subsided after several minutes
- extractionthe product then extracted with diethyl ether (three 200-ml portions)
- washThe combined extracts were washed with saturated sodium bicarbonate solution (200 ml)
- customThe ether was evaporated
Sources & evidence
- ORD record
- ord-a3b1e7a42fc34a7fa897b78579b481d6
- Source dataset
- uspto-grants-1979_09
- Patent number
- US04166915
Reaction notes
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