Thionyl Chloride → HCID 21485202, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11](O)[CH3:12].S(Cl)([Cl:16])=O>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]([Cl:16])[CH3:12]Participants
Procedure
Starting, for example, from 1-(2,4-dimethoxy-phenyl)-ethanol and treating same with thionyl chloride there can be obtained 1-(2,4-dimethoxy-phenyl)-ethyl chloride which can be converted by reaction with potassium cyanide and subsequent methylation with sodium amide and methyl iodide into 2-(2,4-dimethoxy-phenyl)-2-methyl-propionitrile. Alkaline hydrolysis of the nitrile group and subsequent reduction of the carboxyl group with lithium aluminum hydride gives 2-(2,4-dimethoxy-phenyl)-2-methyl-propanol which, by treatment with hydrobromic acid/glacial acetic acid and subsequent cyclization of the resulting 2-(2,4-dihydroxy-phenyl)-2-methyl-propyl bromide with potassium carbonate in acetone, yields 3,3-dimethyl-6-hydroxy-2,3-dihydrobenzofuran.
Sources & evidence
- ORD record
- ord-de579219289e4fa38dfde38aaf029b7e
- Source dataset
- uspto-grants-1977_01
- Patent number
- US04002647
Reaction notes
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