Methanol → 2-(4-(Quinolin-2-ylmethoxy)phenyl)acetic acid

HRID 655359Notes

Reaction equation

HRID 655359 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.CO.C1COCC1.O[Li].O>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

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 58368005Ethyl 2-(4-(quinolin-2-ylmethoxy)phenyl)acetate

Product 1

HCID 145002352-(4-(Quinolin-2-ylmethoxy)phenyl)acetic acidYield 43.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ethyl 2-(4-(quinolin-2-ylmethoxy)phenyl)acetate (25 g, 0.07 mol) in 1:1 (MeOH:THF) (400 mL) were added LiOH.H2O (6.3 g, 0.38 mol) and water (50 mL). The mixture was then stirred at RT for 1 h. The reaction mixture was then concentrated in vacuo. The residue was then acidified with aqueous HCl (1N) and extracted with EtOAc (2×300 mL). The combined organic layers were washed with water, dried over Na2SO4 and concentrated in vacuo to afford 2-(4-(quinolin-2-ylmethoxy)phenyl)acetic acid (9.0 g, 40%) as a solid.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. extractionextracted with EtOAc (2×300 mL)
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e15f687a9b5f4b459707e3516a067da1
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Reaction notes

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