Water → Methyl 2-(5-formyl-2-isobutoxyphenyl)acetate
Reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:2]([CH3:4])[CH3:3].[CH3:17][O:18]C(Cl)Cl.O>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[CH:17]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:1][CH:2]([CH3:4])[CH3:3])=[C:7]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:8]=1)=[O:18]Participants
Procedure
In 10 ml of methylene chloride is dissolved 1.00 g of methyl 2-(2-isobutoxyphenyl)acetate. After successively adding 0.99 ml of titanium tetrachloride and 0.45 ml of α,α-dichloromethyl methyl ether at 5-10° C., the mixture thus obtained is stirred at ambient temperature for 30 minutes. The reaction mixture is added to a mixture of methylene chloride and water, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=95:5) to obtain 0.80 g of methyl 2-(5-formyl-2-isobutoxyphenyl)acetate as a colorless oily product.
Workup
- customthe mixture thus obtained
- customthe organic layer is separated
- customThe organic layer thus obtained
- washis washed with water and saturated aqueous solution of sodium chloride successively
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent is distilled off under reduced pressure
- customThe residue is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=95:5)
Sources & evidence
- ORD record
- ord-219373a5063748759678f03cfdc5f7ab
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07314888B1
Reaction notes
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