1,3-Butadiene → 2,4-Dimethylspiro[5.5]undeca-1,4,8-trien-3-one

HRID 638666Notes

Reaction equation

HRID 638666 reaction equation
CN([CH2:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([OH:12])=[C:7]([CH3:13])[CH:6]=1)C.[CH2:14]=[CH:15][CH:16]=[CH2:17]>C1(C)C=CC=CC=1>[CH3:13][C:7]1[C:8](=[O:12])[C:9]([CH3:11])=[CH:10][C:5]2([CH2:17][CH2:16][CH:15]=[CH:14][CH2:4]2)[CH:6]=1

Participants

4

Reactant 2

HCID 78451,3-ButadieneHCID 39355Phenol, 4-[(dimethylamino)methyl]-2,6-dimethyl-

Product 1

HCID 135314552,4-Dimethylspiro[5.5]undeca-1,4,8-trien-3-oneYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Following the same general procedure as in Example I, 5 mmols of N,N-dimethyl-4-aminomethyl-2,6-dimethylphenol were reacted with 20 mmols of 1,3-butadiene in 40 g of toluene at 189°-205° C. for six hours. GC analysis showed a 78% yield of 2,4-dimethylspiro[5.5]undeca-1,4,8-trien-3-one.

Sources & evidence

ORD record
ord-eec27bd319254a759a5373dcbe27566c
Source dataset
uspto-grants-1985_12
Patent number
US04562294

Reaction notes

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