Potassium Hydroxide → 2-(2-Chlorophenylthio)-6-(1-propenyl)phenol
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH:16]=[CH2:17])[C:10]=1[OH:18].[OH-].[K+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[CH:16][CH3:17])[C:10]=1[OH:18]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
A mixture of 2-(2-chlorophenylthio)-6-allylphenol (32 g) and potassium hydroxide (41 g) in methanol (140 ml) was stirred at 110° C., and methanol was distilled off under ordinal pressure. The remaining mixture was further stirred at 100° C. for an hour, cooled to the ambient temperature and then dissolved in water. The aqueous solution was acidified with conc. hydrochloric acid under ice-water cooling. The resultant oily substance was extracted with diethyl ether, and the extract was washed with water, dried over magnesium sulfate and then evaporated under reduced pressure to give oily 2-(2-chlorophenylthio)-6-(1-propenyl)phenol (31.5 g). This product was subjected to column chromatography on silica gel (450 g) and eluted with a mixture of benzene and n-hexane (1:10) to give the purified oily product (26.3 g).
Workup
- distillationmethanol was distilled off under ordinal pressure
- stirringThe remaining mixture was further stirred at 100° C. for an hour
- temperaturecooled to the ambient temperature
- dissolutiondissolved in water
- extractionThe resultant oily substance was extracted with diethyl ether
- washthe extract was washed with water
- dry with materialdried over magnesium sulfate
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-596164af212841aeb1867634e871400a
- Source dataset
- uspto-grants-1983_01
- Patent number
- US04367238
Reaction notes
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