Hydrochloric Acid → 1-Phenylcyclobutane-1-carbaldehyde
Reaction equation
[C:1]1([C:7]2([C:11]#N)[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.CC[O:16]CC>CCCCCC>[C:1]1([C:7]2([CH:11]=[O:16])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
A 1M solution of diisobutylaliminohydride in hexane (200 ml) was added under nitrogen to a solution of 1-phenyl-1-cyclobutane carbonitrile (31.4 g) in ether (100 ml) at a temperature below -30° C. The temperature was maintained below 0° C. for thirty minutes and 5N hydrochloric acid (200 ml) at a temperature of -10° C. added. The reaction mixture was washed with petroleum ether (b.p. 60°-80° C.) and then warmed to 40° C. The reaction mixture was extracted with petroleum ether (b.p. 60°-80° C.) and the extract dried and evaporated to yield 1-phenyl-1-cyclobutane-carbaldehyde as an oil.
Workup
- temperatureThe temperature was maintained below 0° C. for thirty minutes
- washThe reaction mixture was washed with petroleum ether (b.p. 60°-80° C.)
- extractionThe reaction mixture was extracted with petroleum ether (b.p. 60°-80° C.)
- customthe extract dried
- customevaporated
Sources & evidence
- ORD record
- ord-bc5639b2a3a143de83832d11bb89c933
- Source dataset
- uspto-grants-1985_06
- Patent number
- US04522828
Reaction notes
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