Acetone → 1,1-Diethoxy-3,7-dimethyl-7-hydroxy-3,5-octadiene
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]([CH3:18])=[O:17]>>[CH2:9]([O:8][CH:7]([O:11][CH2:12][CH3:13])[CH2:6][C:5]([CH3:14])=[CH:4][CH:3]=[CH:2][C:16]([CH3:18])([OH:17])[CH3:15])[CH3:10]Participants
3
Procedure
By proceeding as in Example 1, but starting with 6-bromo-3-methyl-1,1-diethoxy-3,5-hexadiene (0.43 g; 1.63 mmol) and an excess of acetone (0.4 g i.e. 4 equivalents), 1,1-diethoxy-3,7-dimethyl-7-hydroxy-3,5-octadiene, or C10 diethyl hydroxyacetal, (0.4 g) is obtained. After hydrolysis and purification by flash chromatography, eluting with a mixture of petroleum ether and diethyl ether (96/4 by volume), this compound yields dehydrocitral (0.121 g). The yield is 49.6%, based on the 6-bromo-3-methyl-1,1-diethoxy-3,5-hexadiene employed. The structure of the product obtained is confirmed by the infrared spectrum and the proton nuclear magnetic resonance spectrum.
Sources & evidence
- ORD record
- ord-54465c82ce7f41ae8edfb9d7e50312e3
- Source dataset
- uspto-grants-1988_11
- Patent number
- US04788344
Reaction notes
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