Hydrochloric Acid → Ethyl 4-(3-cyanophenoxy)-2-butenoate

HRID 747715Notes

Reaction equation

HRID 747715 reaction equation
Br[CH2:2]/[CH:3]=[CH:4]/[C:5]([O:7][CH2:8][CH3:9])=[O:6].[OH:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#[N:15].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl>CN(C)C=O>[C:14]([C:13]1[CH:12]=[C:11]([CH:18]=[CH:17][CH:16]=1)[O:10][CH2:2][CH:3]=[CH:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])#[N:15]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 133943-CyanophenolHCID 5373944Ethyl (E)-4-bromobut-2-enoate

Product 1

HCID 54098496Ethyl 4-(3-cyanophenoxy)-2-butenoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 g (3.9 mmol) of ethyl 4-bromocrotonate, 465 mg (3.9 mmol) of 3-hydroxybenzonitrile, 539 mg (3.9 mmol) of potassium carbonate and 647 mg (3.9 mmol)) of potassium iodide were stirred in N,N-dimethylformamide at room temperature for 3 days. 1 N hydrochloric acid was added to the reaction liquid. After the extraction with ethyl acetate, the extract was washed with 1 N aqueous sodium hydroxide solution and saturated aqueous common salt solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated to obtain the title compound.

Workup

  1. extractionAfter the extraction with ethyl acetate
  2. washthe extract was washed with 1 N aqueous sodium hydroxide solution and saturated aqueous common salt solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-1e09a9720de24a10a2518ff677d1b241
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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