Sulfuric Acid → 2,2-Diphenylcyclopropane-1-carbaldehyde
Reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]1([C:17]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:19][CH:18]2[C:20]#N)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.S(=O)(=O)(O)[OH:29]>CCCCCC.C1(C)C=CC=CC=1>[C:11]1([C:17]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:19][CH:18]2[CH:20]=[O:29])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -40 °C
Procedure
A solution of diisobutylaluminum hydride in hexane (25%; 212 mL) was added over 30 minutes to a solution of 2,2-diphenylcyclopropanecarbonitrile (45.4 g) in dry toluene (400 mL) maintained at -40° C. during the addition. After the reaction had been stirred at room temperature for 1 hour, it was rechilled to 0°-5° C. and 2N sulfuric acid (400 mL) was added dropwise. The two phase system was stirred at ambient temperature for 1 hours then the layers were separated and the aqueous phase was extracted with ethyl acetate (2×300 mL). The organic layers were washed with Rochelle salt solution (5%; 2×200 mL), then were dried (Na2SO4) and evaporated to give 2,2-diphenylcyclopropanecarboxaldehyde as a solid, mp 71°-73° C. A sample was crystallized from benzene-hexane to provide the purified aldehyde, mp 75°-76° C.
Workup
- customwas rechilled to 0°-5° C.
- stirringThe two phase system was stirred at ambient temperature for 1 hours
- customthe layers were separated
- extractionthe aqueous phase was extracted with ethyl acetate (2×300 mL)
- washThe organic layers were washed with Rochelle salt solution (5%; 2×200 mL)
- dry with materialwere dried (Na2SO4)
- customevaporated
Sources & evidence
- ORD record
- ord-ff9682b70c394fba91d026d08aee02a9
- Source dataset
- uspto-grants-1990_05
- Patent number
- US04927826
Reaction notes
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