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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1107425Generated: October 31, 2026

3-Methyl-2-butenoic acid → HCID 18787214, compound

https://huagongshe.com/reaction/1107425

Reaction equation

Participants

RoleNameHCIDCharge
Reactant3-Methyl-2-butenoic acidHCID 10931—
Reactant2-Cyclohexen-1-oneHCID 13594—
ReactantDiethyl aluminum cyanideHCID 16686413—
ReactantHCID 18787233HCID 18787233—
SolventTetrahydrofuranHCID 8028—
ProductHCID 18787214HCID 18787214—

Reaction Steps

The amines where R0 contains a 5,5-dimethyl-3-phenyl-2-cyclohexanol may be prepared substantially as described in Mestres et al., Tetrahedron, volume 50, page 2571 (1994). For example, in a tandem Michael-Dieckmann decarboxylative annulation of trans-βmethylcinnamic acid and 3,3-dimethylacrylic acid, the cyclohexenone was stirred with diethylaluminum cyanide in tetrahydrofuran at room temperature overnight to provide 3-cyano-5,5-dimethyl-3-phenylcyclohexanone which was then hydrogenated over 5% rhodium on alumina to give the corresponding amine.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06060484
Source datasetuspto-grants-2000_05
ORD IDord-19d51c06a6de459bb5c6ad04c4994966
Source noteuspto-grants-2000_05