Hydrochloric Acid → 2-Ethyl-[1,1'-biphenyl]-3-carboxylic acid

HRID 1995133Notes

Reaction equation

HRID 1995133 reaction equation
[CH2:1]([C:3]1[C:8]([C:9](N)=[O:10])=[CH:7][CH:6]=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:2].[OH-:18].[K+].Cl>OCCOCCO.C(OCC)C>[CH2:1]([C:3]1[C:8]([C:9]([OH:18])=[O:10])=[CH:7][CH:6]=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 202706622-Ethyl[1,1'-biphenyl]-3-carboxamide

Product 1

HCID 202706372-Ethyl-[1,1'-biphenyl]-3-carboxylic acidYield 104.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8117Diethylene GlycolSolvent

Procedure

A stirred solution of 2-ethyl-[1,1'-biphenyl]-3-carboxamide (2.1 g, 0.0093 mole) and potassium hydroxide (26.3 g, 0.4 mole) in 175 ml of 2-hydroxyethyl ether was heated at 163° for approximately 18 hours. The reaction mixture was cooled and diluted with 150 ml of ice water. The solution was acidified with concentrated hydrochloric acid to form a precipitate. The precipitate was isolated by filtration and dissolved in diethyl ether; the ethereal solution was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated to give 2-ethyl-[1,1'-biphenyl]-3-carboxylic acid (2.2 g) as a solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customto form a precipitate
  3. customThe precipitate was isolated by filtration
  4. dry with materialthe ethereal solution was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-a4a228e8b5514a63ab0163463c65cf80
Source dataset
uspto-grants-1983_09
Patent number
US04402973

Reaction notes

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