2-Butanone, 4-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)- → HCID 19857690, compound

HRID 1973202Notes

Reaction equation

HRID 1973202 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1[CH2:10][CH2:11][C:12](=[O:14])[CH3:13].CC1C(/C=C/C(C)=O)C(C)(C)CCC1>>[CH3:8][C:4]1([CH3:9])[CH:3]([CH2:10][CH2:11][C:12](=[O:14])[CH3:13])[C:2](=[CH2:1])[CH:7]=[CH:6][CH2:5]1

Participants

3

Reactant 2

HCID 5771262-Butanone, 4-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-HCID 643112236208-32-9

Product 1

HCID 19857690HCID 19857690, compound

Procedure

4-(2,6,6-TRIMETHYL-1,3-CYCLOHEXADIEN-1-YL)-2-BUTANONE HAVING THE STRUCTURE: ##STR2## may be synthesized according to the technique of Wolf and Zink, Volume 56, Helvetica Chimica Acta., Fasc 3 (1973) pp. 1062-1066, or according to Examples I and II of Rowland, U.S. Pat. No. 3,436,421 issued on Apr. 1, 1969 by means of bromination of -dihydroionone followed by debromination. 4-(6,6-dimethyl-2-methylene-3-cyclohexen-1-yl)-2-butanone having the structure: ##STR3## is also produced in this process as a bi-product thereof (B.P. 65° C at 0.15 mm Hg. pressure). 4-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-butanone is also shown to be a bi-product in the cyclization of ionone to beta ionone by Kruk and De Boer in Volume 87 Recueil (1968) pp. 641-654 as an intermediate in preparing other perfumery compounds. The compound having the structure: ##STR4## is disclosed in Japanese Patent No. 7121,015 (Sakan and Isoe)issued June 14, 1971.

Sources & evidence

ORD record
ord-fd26229e140749c8ba22cb1165badd3e
Source dataset
uspto-grants-1976_12
Patent number
US03996296

Reaction notes

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