Hydrochloric Acid → 2-(4-Cyanophenoxy)acetic acid

HRID 2264093Notes

Reaction equation

HRID 2264093 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:17])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1)C.Cl>CO>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:6]([OH:17])=[O:5])=[CH:10][CH:11]=1)#[N:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 207426Ethyl (4-cyanophenoxy)acetate

Product 1

HCID 7360972-(4-Cyanophenoxy)acetic acidYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1 N solution of NaOH (7.6 mL; 7.6 mmol) was added dropwise to a solution of (4-cyanophenoxy)acetic acid ethyl ester B (1.55 g; 7.6 mmol) in MeOH (15 mL). After 1 h the solution was acidified with 1 N HCl (7.6 mL; 7.6 mmol) and evaporated. The residue was taken up with water (20 mL) and extracted with CHCl3 (2×30 mL). The organic phases were evaporated and the crude was purified by flash chromatography to give (4-cyanophenoxy)acetic acid C (0.97 g; 5.5 mmol) as a white solid. Yield 72%.

Workup

  1. customevaporated
  2. extractionextracted with CHCl3 (2×30 mL)
  3. customThe organic phases were evaporated
  4. customthe crude was purified by flash chromatography

Sources & evidence

ORD record
ord-e70cf753fe2c4f7faa89da4d570eaf05
Source dataset
uspto-grants-2010_12
Patent number
US07850947B2

Reaction notes

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