Reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:24]([O:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1)([CH3:26])[CH3:25].C(=O)([O-])O.[Na+]>COC(C)(C)C>[CH3:2][O:3][CH:4]=[CH:32][C:31]1[CH:34]=[CH:35][C:28]([O:27][CH:24]([CH3:26])[CH3:25])=[CH:29][CH:30]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
A suspension of 140 g of methoxymethyl-triphenylphosphonium chloride in 400 ml of tert.-butyl methyl ether is treated with 45 g of potassium tert.-butylate within 5 minutes at 0° C. while gassing with nitrogen and the mixture is stirred for a further 10 minutes. Then, a solution of 41 g of 4-(isopropyloxy)-benzaldehyde in 100 ml of tert.-butyl methyl ether is added dropwise at 0° C. within 30 minutes. The reaction mixture is stirred at room temperature for a further 16 hours and then poured into 750 ml of 0.8N sodium hydrogen carbonate solution. The aqueous phase is separated and back-extracted with diethyl ether. The organic phase is washed neutral with water, dried over magnesium sulphate and concentrated. The residue is suspended in 800 ml of hexane. After cooling to 0° C. the triphenylphosphine oxide is filtered off and the filtrate is concentrated. Chromatography of the residue on silica gel with hexane/ethyl acetate (vol. 9:1) gives 45 g of pure 1-methoxy-2-(4-[isopropoxy]phenyl)ethene.
Workup
- stirringThe reaction mixture is stirred at room temperature for a further 16 hours
- customThe aqueous phase is separated
- extractionback-extracted with diethyl ether
- washThe organic phase is washed neutral with water
- dry with materialdried over magnesium sulphate
- concentrationconcentrated
- filtrationis filtered off
- concentrationthe filtrate is concentrated
Sources & evidence
- ORD record
- ord-f7e197db34504310b76a939086711b95
- Source dataset
- uspto-grants-1995_02
- Patent number
- US05393458
Linked notes
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