Diethyl Ether → 5-Norbornene-2-carboxylic acid
Reaction equation
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.[C:6]([OH:10])(=[O:9])C=C.[CH2:11](OCC)[CH3:12]>>[CH:2]12[CH2:1][CH:5]([CH:11]=[CH:12]1)[CH2:4][CH:3]2[C:6]([OH:10])=[O:9]Participants
4
Procedure
Freshly distilled cyclopenta-1,3-diene (66.11 g) was added to a solution of freshly distilled acrylic acid (73 g, inhibited with p-methoxyphenol) and diethyl ether (75 ml). The solution had a temperature between 5° C. and 10° C. The exothermic reaction that ensued was controlled by an ice bath. The cyclopentadiene was added to the solution over a period of 30 minutes and after all the cyclopentadiene had been added, the solution was allowed to warm to ambient temperature. After a reaction period of 4 hours, gas chromatographic (GC) analysis indicated a yield of 100 percent of theory of the carboxylic acid. The carboxylic acid was recovered from the diethyl ether by vacuum distillation.
Workup
- customa temperature between 5° C. and 10° C
- customThe exothermic reaction
- customthat ensued was controlled by an ice bath
- customAfter a reaction period of 4 hours, gas chromatographic (GC) analysis
- distillationThe carboxylic acid was recovered from the diethyl ether by vacuum distillation
Sources & evidence
- ORD record
- ord-8e1bb9a1e4094fa89eae3c1177ed9ce8
- Source dataset
- uspto-grants-1979_09
- Patent number
- US04166915
Reaction notes
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