HCID 58194293, compound → HCID 58194347, compound

HRID 68526Notes

Reaction equation

HRID 68526 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([CH:25]=[CH:26][CH:27]=1)[C:14]([C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([OH:20])=[O:19])=O>[OH-].[Na+].[Zn].S([O-])([O-])(=O)=O.[Cu+2]>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([CH:25]=[CH:26][CH:27]=1)[CH2:14][C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([OH:20])=[O:19]

Participants

5

Reactant 1

HCID 58194293HCID 58194293, compound

Product 1

HCID 58194347HCID 58194347, compoundYield 94.7%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24462Copper SulfateCatalystHCID 14798Sodium HydroxideSolvent

Procedure

First, 121 g of 2-[3-(2-naphthyl)benzoyl]benzoic acid were dissolved in 10 L of a 1N sodium hydroxide solution, and then a zinc powder activated with an aqueous solution of copper sulfate was added to the solution. The reaction solution was stirred for 50 hours under reflux. After having been cooled to room temperature, the reaction solution was filtrated. The filtrate was acidified, and then the resultant solid was washed with boiling water. Thus, 110 g of 2-[3-(2-naphthyl)benzyl]benzoic acid were obtained (in 90% yield).

Workup

  1. additionwas added to the solution
  2. temperatureunder reflux
  3. filtrationthe reaction solution was filtrated
  4. washthe resultant solid was washed with boiling water

Sources & evidence

ORD record
ord-26e34821b2e84db6980d9c9b618027e3
Source dataset
uspto-grants-2014_09
Patent number
US08822041B2

Reaction notes

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