Sodium Hydroxide → 2-cyclohexyl-2-[4-(quinolin-2-ylmethoxy)phenyl]acetic Acid

HRID 1708495Notes

Reaction equation

HRID 1708495 reaction equation
C[O:2][C:3](=[O:29])[CH:4]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)=[CH:7][CH:6]=1.[OH-].[Na+]>CO>[CH:23]1([CH:4]([C:5]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)=[CH:7][CH:6]=2)[C:3]([OH:29])=[O:2])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 146748362-Cyclohexyl-2-[4-(quinolin-2-yl-methoxy)phenyl]acetic acid methyl ester

Product 1

HCID 111997052-cyclohexyl-2-[4-(quinolin-2-ylmethoxy)phenyl]acetic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the above ester and 1N sodium hydroxide (3 ml) in methanol (12 ml) was refluxed at 50° C. for 72 h and then concentrated in vacuo. To the residue was added water (5 ml) and 10% citric acid to pH 3, and the resulting solid was filtered crystallized from methanol to provide 500 mg of 2-cyclohexyl-2-[4-(quinolin-2-ylmethoxy)phenyl]acetic acid.

Workup

  1. concentrationconcentrated in vacuo
  2. additionTo the residue was added water (5 ml) and 10% citric acid to pH 3
  3. filtrationthe resulting solid was filtered
  4. customcrystallized from methanol

Sources & evidence

ORD record
ord-ee5dde2728bc439695c026a75e7239f2
Source dataset
uspto-grants-1994_10
Patent number
US05358955

Reaction notes

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