Sulfuric Acid → HCID 12815949, compound
Reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([S:10][C:11]([F:14])([F:13])[F:12])=[CH:6][C:3]=1[CH2:4][OH:5].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].S(=O)(=O)(O)O>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.ClCCl.O>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([S:10][C:11]([F:14])([F:12])[F:13])=[CH:6][C:3]=1[CH:4]=[O:5]Participants
Procedure
Triethylbenzylammonium chloride (3.6 g) is added to a solution of 39.9 g of crude 2-chloro-5-(trifluoromethylthio) benzyl alcohol in 400 ml of dichloromethane and the mixture is treated dropwise at 15°-20° C. with a solution of 20.6 g of potassium dichromate in 270 ml of water containing 135 ml of sulfuric acid. The mixture is stirred for 4 hours at room temperature and allowed to stand overnight. The aqueous layer is then separated and the organic layer washed with water and a 5% sodium hydroxide solution, dried with magnesium sulfate and evaporated. The residue is distilled in vacuo. There are obtained 34.1 g of crude 2-chloro-5-(trifluoromethylthio)benzaldehyde boiling at 120°-130° C./2 kPa. According to the 1H-NMR spectrum the product consists of approximately 80% of the named compound and the remainder is the position isomer. In this state the substance is suitable for further processing.
Workup
- waitto stand overnight
- customThe aqueous layer is then separated
- washthe organic layer washed with water
- dry with materiala 5% sodium hydroxide solution, dried with magnesium sulfate
- customevaporated
- distillationThe residue is distilled in vacuo
Sources & evidence
- ORD record
- ord-a4c90e2160364c8da612467ed4e2d9bf
- Source dataset
- uspto-grants-1984_02
- Patent number
- US04431808
Reaction notes
Loading…