Hydrochloric Acid → 2-((4-(Dimethylamino)-3,5-bis(1-methylethyl)phenyl)thio)-hexanoic acid
Reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1[C:8]([CH:9]([CH3:11])[CH3:10])=[CH:7][C:6]([S:12]C#N)=[CH:5][C:4]=1[CH:15]([CH3:17])[CH3:16].SC1C=CC=CC=1O.[OH-].[Na+].Br[CH:30]([CH2:34][CH2:35][CH2:36][CH3:37])[C:31]([OH:33])=[O:32].Cl>>[CH3:18][N:2]([CH3:1])[C:3]1[C:4]([CH:15]([CH3:17])[CH3:16])=[CH:5][C:6]([S:12][CH:30]([CH2:34][CH2:35][CH2:36][CH3:37])[C:31]([OH:33])=[O:32])=[CH:7][C:8]=1[CH:9]([CH3:11])[CH3:10]Participants
Procedure
To the toluene solution containing the mercaptophenol prepared above 200 ml. of 20% sodium hydroxide and 7.4 grams of 2-bromo-hexanoic acid were added. The reaction mass was stirred at room temperature for about one hour. The mixture was then treated with 100 ml. of 1 N hydrochloric acid. The resulting layers were separated and the toluene was washed twice or until neutral. The organic layers were dried over Na2SO4 and evaporated to leave a light yellow oil weighing 13.4 grams which crystallized on standing. The crystals of 2-((4-(dimethylamino)-3,5-bis(1-methylethyl)phenyl)thio)-hexanoic acid were washed with cold pentane and sucked dry on a suction filter to give 3.14 grams of product. The melting point was found to be 66°-68° C. Infrared and NMR analysis confirmed the structure.
Workup
- customprepared above 200 ml
- additionThe mixture was then treated with 100 ml
- customThe resulting layers were separated
- washthe toluene was washed twice
- dry with materialThe organic layers were dried over Na2SO4
- customevaporated
- customto leave a light yellow oil
- customcrystallized
- washThe crystals of 2-((4-(dimethylamino)-3,5-bis(1-methylethyl)phenyl)thio)-hexanoic acid were washed with cold pentane
- customsucked dry on a suction
- filtrationfilter
Sources & evidence
- ORD record
- ord-ede1ac7fe3cd44abaf780e2387250896
- Source dataset
- uspto-grants-1978_07
- Patent number
- US04103027
Reaction notes
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