Cyanoacetic acid → 3-Carene

HRID 1856377Notes

Reaction equation

HRID 1856377 reaction equation
C(CC(O)=O)#N.C([CH:9]1[CH2:14][CH:13]2[C:15]([CH3:17])([CH3:16])[CH:12]2[CH2:11][CH:10]1[CH3:18])=O>>[CH:12]12[C:15]([CH3:17])([CH3:16])[CH:13]1[CH2:14][CH:9]=[C:10]([CH3:18])[CH2:11]2

Participants

3

Reactant 2

HCID 9740Cyanoacetic acidHCID 133790334,7,7-Trimethylbicyclo[4.1.0]heptane-3-carbaldehyde

Product 1

HCID 260493-Carene

Procedure

The condensation of cyanoacetic acid and 4-formylcarane obtained via the Prins reaction of 3-carene as described in Annalen 613, p. 43 (1958), was carried out according to the procedure of Example 3A. Yield 73% of the isomeric mixture 3-(3,7,7-trimethylbicyclo [4.1.0]heptylidene-4)propanenitrile and 3-(3,7,7-trimethylbicyclo [4.1.0]heptyl-4)acrylonitrile, b.p. 99°-103° C. at 0.6 mm Hg, nD20 =1.4950, with metallic, woody, rosy odour.

Sources & evidence

ORD record
ord-e7fb0a07ed304bbbb871660fab7aa103
Source dataset
uspto-grants-1980_08
Patent number
US04219449

Reaction notes

Loading…