Cyanoacetic acid → HCID 54086143, compound

HRID 232338Notes

Reaction equation

HRID 232338 reaction equation
[CH:1]12[CH2:15][CH2:14]O[CH:12]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2.C1(=O)CCCCCCCCCCC1.C(CC(O)=O)#[N:30]>>[C:1]1([CH2:15][C:14]#[N:30])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

4

Reactant 3

HCID 9740Cyanoacetic acidHCID 13246CyclododecanoneHCID 14687820tetradecahydrocyclododeca[b]furan

Product 1

HCID 54086143HCID 54086143, compound

Procedure

13-oxabicyclo[10.3.0]pentadecane, a valuable ambergris fragrance, is prepared by reacting cyclododecanone with cyanoacetic acid in the presence of a Knoevenagel catalyst to form cyclododecenylacetonitrile, the nitrile is hydrolyzed to cyclododecenylacetic acid, and the acid is cyclized to the lactone, and the lactone is reduced to the corresponding diol which is cyclized to 13-oxabicyclo[10.3.0]pentadecane.

Sources & evidence

ORD record
ord-6443ebba35f7430bb775b16189d70029
Source dataset
uspto-grants-1989_07
Patent number
US04851552

Reaction notes

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