Sodium Hydroxide → 2'-Methyl-biphenyl-2,4'-dicarboxylic acid

HRID 1799021Notes

Reaction equation

HRID 1799021 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[C:13]([C:18]([O:20]CC)=[O:19])=[CH:14][CH:15]=[CH:16][CH:17]=1.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[C:13]([C:18]([OH:20])=[O:19])=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Conditions

Temperature
100 °C

Procedure

A mixture of 2-ethyl 4′-methyl 2′-methyl-biphenyl-2,4′-dicarboxylate (2.404 g), ethanol (12 ml) and 4N aqueous sodium hydroxide solution (6 ml) was stirred at 100° C. overnight. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and water (50 ml) was added to the obtained residue. This mixture was adjusted to pH 1 with 6N hydrochloric acid (5 ml), ethanol (10 ml) was added, and the mixture was stirred at room temperature for 10 min. This suspension was filtered, the obtained solid was washed with 20v/v % ethanol-water (10 ml), air-dried, and dried under reduced pressure at 80° C. to give the title compound (1.957 g, 95%).

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure, and water (50 ml)
  3. additionwas added to the obtained residue
  4. additionwas added
  5. stirringthe mixture was stirred at room temperature for 10 min
  6. filtrationThis suspension was filtered
  7. washthe obtained solid was washed with 20v/v % ethanol-water (10 ml)
  8. customair-dried
  9. customdried under reduced pressure at 80° C.

Sources & evidence

ORD record
ord-580bfe9b8add468298624df49db273e5
Source dataset
uspto-grants-2013_01
Patent number
US08343994B2

Reaction notes

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