Hydrochloric Acid → 136946-81-1

HRID 1250757Notes

Reaction equation

HRID 1250757 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[Cl-].[Cl-].[C:8]1([CH3:15])[C:9]([CH3:14])=[CH:10][CH:11]=[CH:12][CH:13]=1.C([N-][CH:20]([CH3:22])[CH3:21])(C)C.[Li+].[CH:24](NC(C)C)(C)C.Cl.O1[CH2:36][CH2:35][CH2:34][CH2:33]1>CCCCCC>[CH:14]1([CH2:4][CH2:3][CH:2]2[C:1]3[C:35](=[CH:36][CH:22]=[CH:20][CH:21]=3)[CH:34]=[CH:33]2)[C:9]2[C:8](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:24]1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 8028Tetrahydrofuran3×HCID 2724682Lithium diisopropylamideHCID 18326907HCID 18326907, compoundHCID 178418339Butyllithium2×

Product 1

HCID 2733355136946-81-1

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1,4-bis(phenylsulfonyl)butane (16.9 g, 50.0 mmol) obtained in the above-mentioned (1) was dissolved in tetrahydrofuran (500 ml). After cooling to 0° C., 128 ml (n-butyllithium: 205 mmol) of a hexane solution having an n-butyllithium concentration of 1.6 mol/l was added. After 1 hour, a tetrahydrofuran solution (500 mol) of o-xylene dichloride (17.9 g, 102 mmol) was added to the solution which was being vigorously stirred, followed by stirring at room temperature for 2 hours. Next, the solution was cooled to −78° C., and a tetrahydrofuran solution (250 ml) of lithiumdiisopropylamide prepared from a hexane solution (256 ml) having an n-butyllithium concentration of 1.6 mol/l and diisopropylamine (57.7 ml) was slowly added thereto. After 30 minutes, 5% hydrochloric acid (200 ml) was added at 0C. The solution was extracted with ethyl acetate, and the collected organic layer was dried over anhydrous magnesium sulfate. After concentration under reduced pressure, Soxhlet extraction using hexane was carried out to obtain a desired product. Its yield was 2.0 g, i.e., 15%.

Workup

  1. additionwas added
  2. stirringby stirring at room temperature for 2 hours
  3. temperatureNext, the solution was cooled to −78° C.
  4. additionwas slowly added
  5. waitAfter 30 minutes
  6. extractionThe solution was extracted with ethyl acetate
  7. dry with materialthe collected organic layer was dried over anhydrous magnesium sulfate
  8. concentrationAfter concentration
  9. extractionunder reduced pressure, Soxhlet extraction

Sources & evidence

ORD record
ord-229bc388d08f491c834c98f15056e862
Source dataset
uspto-grants-2002_01
Patent number
US06339135B1

Reaction notes

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