Potassium Hydroxide → 2-(4-(Quinolin-2-ylmethoxy)phenyl)acetic acid

HRID 655407Notes

Reaction equation

HRID 655407 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22]CC)=[O:21])=[CH:15][CH:14]=1.[OH-].[K+]>C(O)C.O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 58368005Ethyl 2-(4-(quinolin-2-ylmethoxy)phenyl)acetate

Product 1

HCID 145002352-(4-(Quinolin-2-ylmethoxy)phenyl)acetic acidYield 95.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of ethyl 2-(4-(quinolin-2-ylmethoxy)phenyl)acetate (38.0 g, 106.741 mmol) in ethanol (200 mL) and water (100 mL) was added KOH (23.9 g, 426.964 mmol) at room temperature. The mixture was stirred at RT for 4 h and after complete consumption of starting material as monitored by TLC, the reaction mixture was diluted with water (50 mL) and acidified using 1 N HCl at 0° C. The aqueous layer was extracted with EtOAc (2×150 mL) and the combined organic extracts were washed with water (50 mL) and brine (50 mL), dried over anhydrous Na2SO4, and evaporated in vacuo to afford 2-(4-(quinolin-2-ylmethoxy)phenyl)acetic acid (30.0 g, 95%) as a white solid.

Workup

  1. customafter complete consumption of starting material
  2. additionthe reaction mixture was diluted with water (50 mL)
  3. customat 0° C
  4. extractionThe aqueous layer was extracted with EtOAc (2×150 mL)
  5. washthe combined organic extracts were washed with water (50 mL) and brine (50 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-8e8c32edfcaa4a34bbb1f815a9d6a3b6
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Reaction notes

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