Hydrochloric Acid → HCID 58246301, compound

HRID 1850830Notes

Reaction equation

HRID 1850830 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:11][C:10]([O:12]C)=[CH:9]2)=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl.[OH-].[Na+]>CC(C)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:14]#[N:15])[CH2:9][C:10](=[O:12])[CH2:11]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 58246184HCID 58246184, compound

Product 1

HCID 58246301HCID 58246301, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

1-(4-Chloro-phenyl)-3-methoxy-cyclobut-2-enecarbonitrile (8.80 g, 40.1 mmol), 4-toluene sulfonic acid (2.30 g, 12.1 mmol), and 2 N HCl were dissolved in acetone/water 100:10 (110 ml) and stirred for 10 h under reflux. The reaction mixture was alkalized with aqueous NaOH and extracted with ethyl acetate. The combined organic layers were washed with water and subsequently with saturated sodium chloride solution and dried with sodium sulphate. The product was obtained as an orange oil (7.40 g, 36.0 mmol) that was sufficiently pure for the next step.

Workup

  1. temperatureunder reflux
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with water and subsequently with saturated sodium chloride solution
  4. dry with materialdried with sodium sulphate

Sources & evidence

ORD record
ord-5236f712e7bb4318a4e4812f1303fb72
Source dataset
uspto-grants-2015_02
Patent number
US08957089B2

Reaction notes

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