Phosphorus oxychloride → 4-t-Amylbenzenesulphonyl chloride
Reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([O-:15])(=O)=[O:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[K+].P(Cl)(Cl)([Cl:19])=O>O>[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([Cl:19])(=[O:15])=[O:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 170 °C
Procedure
A mixture of potassium 4-n-pentylbenzene sulfonate (65 g, 0.243 m) and phosphoryl chloride (75 g, 0.492 m) was heated to approximately 170° C. with stirring until the reaction mixture became less viscous. Heating continued for approximately one hour. The hot reaction mixture was poured into cold water (1600 ml) and the reaction product was extracted with chloroform (2×600 ml). The extract was washed with water until it was neutralized and dried over anhydrous sodium sulfate. The solvent (chloroform) was evaporated and the extract was vacuum-distilled to give 4-n-pentylbenzenesulfonyl chloride (52 g, 87%, boiling point 132°-134° C./0.3 mm).
Workup
- temperatureHeating
- extractionthe reaction product was extracted with chloroform (2×600 ml)
- washThe extract was washed with water until it
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent (chloroform) was evaporated
- distillationthe extract was vacuum-distilled
Sources & evidence
- ORD record
- ord-c6aed0239b504ec59d76bb89d9c7ee03
- Source dataset
- uspto-grants-1984_01
- Patent number
- US04424372
Reaction notes
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