I2-Ionone → HCID 54275784, compound

HRID 845886

Reaction equation

Br[CH:2]=[CH:3][CH:4]=[C:5]([CH3:14])[CH2:6][CH:7]([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10].[CH3:15][C:16]1[CH2:21][CH2:20][CH2:19][C:18]([CH3:23])([CH3:22])[C:17]=1/[CH:24]=[CH:25]/[C:26]([CH3:28])=[O:27]>>[CH3:15][C:16]1[CH2:21][CH2:20][CH2:19][C:18]([CH3:22])([CH3:23])[C:17]=1[CH:24]=[CH:25][C:26]([CH3:28])([OH:27])[CH:2]=[CH:3][CH:4]=[C:5]([CH3:14])[CH2:6][CH:7]([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10]

Participants

Reactant 2

HCID 638014I2-Ionone

HCID 54085110HCID 54085110, compound

Product 1

HCID 54275784HCID 54275784, compoundYield 73%

Procedure

The procedure is as in Example 1, but employs 6-bromo-3-methyl-1,1-diethoxy-3,5-hexadiene (0.56 g; 2.12 mmol) and β-ionone (0.33 g; 1.716 mmol, i.e. 0.8 equivalent). After flash chromatography, 9-(2,6,6-trimethyl-1cyclohexenyl)-1,1-diethoxy-3,7-dimethyl-7-hydroxy-3,5,8-nonatriene, or C20 diethyl hydroxyacetal, (0.47 g) is obtained. The yield is 73%. The structure of the product obtained is confirmed by the infrared spectrum and the proton nuclear magnetic resonance spectrum.

Sources & evidence

ORD record: ord-39dc048a99714633826056e20b56f09e
Source dataset: uspto-grants-1988_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04760193

Linked notes

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