Methane, dichloromethoxy- → Ethyl 2-(4-Formylphenyl)-2-Methylpropionate
Reaction equation
[C:1]1([C:7]([CH3:14])([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][O:16]C(Cl)Cl.S(=O)(O)[O-].[Na+]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH:15]([C:4]1[CH:5]=[CH:6][C:1]([C:7]([CH3:13])([CH3:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:2][CH:3]=1)=[O:16]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 5 °C
Procedure
Ethyl 2-phenyl-2-methylpropionate (10 g) was dissolved in 50 mL of dichloromethane and cooled to 5° C. Titanium tetrachloride (10.5 mL) and 1,1-dichloromethyl methyl ether (7.5 mL) were added and the mixture was stirred at room temperature for 60 hours. The resulting dark solution was diluted with 50 mL of dichloromethane and washed twice with 50 mL of water. The organic solution was concentrated to give an oil which was treated with 30 mL of saturated aqueous sodium bisulfite solution for 12 hours. The precipitate was collected by filtration, washed with hexane, suspended in ethyl acetate and treated with excess potassium carbonate. The organic phase was separated, dried with sodium sulfate and stripped to provide 2 g of product.
Workup
- washwashed twice with 50 mL of water
- concentrationThe organic solution was concentrated
- customto give an oil which
- filtrationThe precipitate was collected by filtration
- washwashed with hexane
- additiontreated with excess potassium carbonate
- customThe organic phase was separated
- dry with materialdried with sodium sulfate
Sources & evidence
- ORD record
- ord-fff4dd3e751544cf9aef43c86e9404fb
- Source dataset
- uspto-grants-2000_11
- Patent number
- US06147217
Reaction notes
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