Carbon Dioxide → 3-(Chloromethoxy)-1,1,1,2,2-pentafluoropropane
Reaction equation
[F:1][C:2]([F:10])([C:6]([F:9])([F:8])[F:7])[CH2:3][O:4][CH3:5].C(=O)=O.S(Cl)([Cl:17])(=O)=O>>[F:1][C:2]([F:10])([C:6]([F:9])([F:8])[F:7])[CH2:3][O:4][CH2:5][Cl:17]Participants
Conditions
- Temperature
- 33 °C
Procedure
Methyl 2,2,3,3,3-pentafluoropropyl ether (225g, 1.37 mole) in a flask fitted with a dry ice cooled condensor and moisture trap was stirred, heated to 33°C, irradiated with ultraviolet light, and sulfuryl chloride (174 g, 1.29 mole) was added dropwise. The reaction temperature dropped to about 0°C as SO2 returned from the condensor. The condensor was allowed to warm gradually to permit SO2 to escape and the reaction temperature to rise to about 33°C to complete the chlorination. The product was washed with ice cold water then with dilute sodium hydroxide solution to remove SO2 and dried to give 250 g of crude XXVII. This was fractionally distilled to give XXVII, b760 87.1-88.5; yield 159 g, purity 92% by GLC. The structure of XXVII was confirmed by proton NMR spectroscopy.
Workup
- additionwas added dropwise
- additionThe reaction temperature dropped to about 0°C as SO2
- temperatureto warm gradually
- customto rise to about 33°C
- washThe product was washed with ice cold water
- customwith dilute sodium hydroxide solution to remove SO2
- customdried
Sources & evidence
- ORD record
- ord-f798dd15bbd84965b7208df5684f90f1
- Source dataset
- uspto-grants-1976_03
- Patent number
- US03943256
Reaction notes
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