Hydrochloric Acid → HCID 13199339, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Al].[H][H].[CH3:12][S:13]SC.Cl>C1CCCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([S:13][CH3:12])[CH:3]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 152 °C
Procedure
A mixture of para-chlorophenol (100 grams, 0.78 moles) and cyclohexane (50 ml) was distilled free of cyclohexane to remove any residual water in the para-chlorophenol. The para-chlorophenol was heated at 160° to 180° C. and aluminum turnings (1.5 grams, 0.06 moles) were slowly added. After cessation of hydrogen evolution, methyldisulfide (46 ml) was added to the mixture and heated at reflux (ca. 152° C.) overnight. The temperature was then increased to 180° C. for 2 additional hours. The mixture was hydrolyzed by the addition of b 1N HCl, extracted with diethyl ether and dried over sodium sulfate. Concentration and distillation through a packed column gave, after removal of the para-chlorophenol, 52.25 grams of 4-chloro-2-(methylthio)-phenol product. The result was confirmed by NMR analysis, the overall yield being 55 percent.
Workup
- distillationwas distilled free of cyclohexane
- customto remove any residual water in the para-chlorophenol
- temperatureThe para-chlorophenol was heated at 160° to 180° C.
- temperatureheated
- temperatureThe temperature was then increased to 180° C. for 2 additional hours
- extractionextracted with diethyl ether
- dry with materialdried over sodium sulfate
- concentrationConcentration and distillation through a packed column
- customgave
- customafter removal of the para-chlorophenol, 52.25 grams of 4-chloro-2-(methylthio)-phenol product
- customthe overall yield
Sources & evidence
- ORD record
- ord-bc0a8beb975d468e9782fcda1b3b9109
- Source dataset
- uspto-grants-1982_04
- Patent number
- US04324920
Reaction notes
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