Benzene → HCID 53675371, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:13])[C:6](=[C:9]([O:11][CH3:12])[CH:10]=1)[CH:7]=O.[C:14]([CH2:17][CH:18]=[PH2][PH3][PH4])([OH:16])=[O:15].[CH:22]1C=CC=C[CH:23]=1>>[CH2:22]([O:16][C:14](=[O:15])[C:17]([CH3:18])=[CH:7][C:6]1[C:9]([O:11][CH3:12])=[CH:10][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[OH:13])[CH3:23]Participants
Procedure
4,6-Dimethoxysalicylaldehyde (30.0 g, 165 mmol; Aldrich Inc.) and carboxyethylidene-triphosphorane (60.0 g, 166 mmol; Aldrich Inc.) were stirred in 300 ml of anhydrous benzene at room temperature overnight under a nitrogen atmosphere and the reaction was allowed to complete, during which period the reaction was conducted in a dark room. Then, the benzene solvent was removed in vacuo to give a crudely purified product. The resulting crude product was crudely purified by silica gel column chromatography (hexane/ethyl acetate 1:1 as a developing solvent) to give a mixture of cis- and trans-isomers. The thus obtained mixture was purified by column chromatography using aminopropyl-modified silica gel (300 g of NHDM-1020 silica gel available from Fuji Silicia Chemicals Co. Ltd; n-hexane/ethyl acetate 2:1 which elutes only the cis-isomer and chloroform/methanol 4:1 which elutes only the trans-isomer) to give 35.4 g of the desired product in 81% yield.
Workup
- customThen, the benzene solvent was removed in vacuo
- customto give a crudely purified product
- customThe resulting crude product was crudely purified by silica gel column chromatography (hexane/ethyl acetate 1:1 as a developing solvent)
- customto give
- additiona mixture of cis- and trans-isomers
- customThe thus obtained mixture was purified by column chromatography
Sources & evidence
- ORD record
- ord-5ffe5c402681412bb9e5614fdbfa621e
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06207365B1
Reaction notes
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