Cuminaldehyde → 1-Methoxy-2-[4-(1-methylethyl)phenyl]-ethene
Reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[CH:29]([C:32]1[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=1)([CH3:31])[CH3:30].[Cl-].[Na+]>C(OCC)C>[CH3:2][O:3][CH:4]=[CH:36][C:35]1[CH:38]=[CH:39][C:32]([CH:29]([CH3:31])[CH3:30])=[CH:33][CH:34]=1Participants
Procedure
27.7 g of methoxymethyltriphenylphosphonium chloride is introduced into 350 ml of diethyl ether under nitrogen. At 0° C., 38.8 ml of n-butyllithium solution (1.6 M in hexane) is added in drops, and it is stirred for one hour at room temperature. 12 g of 4-isopropylbenzaldehyde in 50 ml of diethyl ether is now added, and it is stirred for one more hour. Sodium chloride solution is added to the reaction mixture, extracted with ethyl acetate, dried on sodium sulfate and concentrated by evaporation. After chromatography on silica gel with ethyl acetate/hexane, 8.1 g of 1-methoxy-2-[4-(1-methylethyl)phenyl]-ethene 42 (E,Z-mixture) is obtained as a colorless oil, which is dissolved in 200 ml of acetone and stirred under nitrogen with 10 ml of 2N hydrochloric acid overnight. Sodium chloride solution is added, extracted with ethyl acetate, dried on sodium sulfate and concentrated by evaporation. Chromatographic purification on silica gel with ethyl acetate/hexane yields 5.1 g of title compound 43 as a colorless oil.
Workup
- stirringit is stirred for one more hour
- extractionextracted with ethyl acetate
- customdried on sodium sulfate
- concentrationconcentrated by evaporation
Sources & evidence
- ORD record
- ord-8fbd65d71930436d8b1f61d49c76feac
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06642218B2
Reaction notes
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