Hydrochloric Acid → HCID 14976589, compound

HRID 871051Notes

Reaction equation

HRID 871051 reaction equation
C([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13].[C:14]1(=O)[O:19][C:17](=[O:18])[CH2:16][CH2:15]1.Cl>C1COCC1.O>[Cl:6][C:7]1[C:8]([Cl:13])=[CH:9][CH:10]=[CH:11][C:12]=1[CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 72391,2-DichlorobenzeneHCID 7922Succinic anhydrideHCID 178418339Butyllithium2×

Product 1

HCID 14976589HCID 14976589, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

In a 100 ml three necked RB flask equipped with a nitrogen gas inlet and an additional funnel, was taken 4 ml of n-butyl lithium (4 ml, 1.8 M in hexanes). Then 10 ml of dry THF was added and the reaction mixture was kept in −80° C. for 0.5 h. A solution of orthodichlorobenzene (0.01 mol, 1.47 g) in 10 ml THF was added in drops by the additional funnel to the n-butyl lithium solution for the period of 10 minutes with keeping the temperature below −78° C. The mixture was stirred for half an hour to form a pale yellow color. Then a solution of succinic anhydride 1 g (0.01 mol) in 10 ml THF was added slowly for the period of 15 minutes. As the addition continued the reaction mixture turned to yellow color. After one hour water 20 ml was added to quench the reaction and acidified with 5 N HCl. It was then extracted with DCM. The organic layer was dried and evaporated to give the required product as oil which was recrystallized from toluene. LCMS analysis revealed the formation of the product. m/e: 246.98

Workup

  1. customthe temperature below −78° C
  2. customto form a pale yellow color
  3. additionAs the addition
  4. customto quench
  5. customthe reaction
  6. extractionIt was then extracted with DCM
  7. customThe organic layer was dried
  8. customevaporated

Sources & evidence

ORD record
ord-113ffee5a23c4f8fab39a496d876f929
Source dataset
uspto-grants-2015_03
Patent number
US08969573B2

Reaction notes

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