Water → HCID 17910497, compound

HRID 1428805Notes

Reaction equation

HRID 1428805 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:15])[C:10]([O:12]CC)=[O:11])=[CH:5][C:4]=1[CH3:16])#[N:2].O1CCCC1.O.[OH-].[Na+]>C(OC(=O)C)C.C(O)(=O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:15])[C:10]([OH:12])=[O:11])=[CH:5][C:4]=1[CH3:16])#[N:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86679386HCID 86679386, compound

Product 1

HCID 17910497HCID 17910497, compoundYield 120.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of ethyl 2-(4-cyano-3-methylphenyl)propanoate (1.05 g, 4.82 mmol) in co-solvent with tetrahydrofuran and water (1:1) were added sodium hydroxide (482 mg, 12.06 mmol). The reaction mixture was stirred for overnight at room temperature, then acidified to pH 3˜4 with acetic acid. The residue was diluted with ethylacetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude 2-(4-cyano-3-methylphenyl)propanoic acid (1.1 g) was obtained as 99% yield.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate removed in vacuo

Sources & evidence

ORD record
ord-fba315152d9648cfaee2d49a8e2d76ca
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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