4-Methylbenzaldehyde → HCID 53981355, compound
Reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[C:10]([C:14](Cl)(Cl)[Cl:15])([F:13])([F:12])[F:11].C(OC(=O)C)(=O)C>CN(C=O)C.O.[Zn]>[Cl:15][C:14]([C:10]([F:13])([F:12])[F:11])=[CH:7][C:4]1[CH:5]=[CH:6][C:1]([CH3:9])=[CH:2][CH:3]=1Participants
Procedure
12 g of p-tolualdehyde dissolved in 20 cc of DMF and 7.5 g of Zn are charged to a flask of 250 ml of capacity. 2.5 g of CF3CCl3 is dropwise added and the resulting reaction mixture is slightly heated until the reaction turns into strongly exothermic. Then 10 g of CF3CCl3 dissolved in 100 cc of DMF is dropwise added and the resulting mixture is stirred at room temperature for 4 hours. 10 cc of acetic anhydride and 13 g of Zn are then added. After 2 hours at room temperature, the reaction mixture is poured in acidic water and is extracted three times with ether; the ether phases are combined with one another, and are washed with a saturated solution of sodium bicarbonate, and with brine, and are then thoroughly dried and evaporated. The raw reaction product is chromatographed on silica (98/2 hexane/ethyl acetate). 11.5 g of 4-(2-chloro-3,3,3-trifluoroprop-1-enyl)-toluene is obtained.
Workup
- customthe resulting reaction mixture
- temperatureis slightly heated until the reaction
- additionis dropwise added
- waitAfter 2 hours at room temperature
- extractionis extracted three times with ether
- washare washed with a saturated solution of sodium bicarbonate
- dry with materialwith brine, and are then thoroughly dried
- customevaporated
- customThe raw reaction product
- customis chromatographed on silica (98/2 hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-a978f59029d24c7a8703d54b15d284c6
- Source dataset
- uspto-grants-1992_12
- Patent number
- US05169848
Reaction notes
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