Sodium Hydroxide → HCID 58188126, compound

HRID 1845151Notes

Reaction equation

HRID 1845151 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[C:10]([C:18]([O:20]C)=[O:19])[CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH3:17][O:16][C:14]([C:12]1[CH:11]=[C:10]([C:18]([OH:20])=[O:19])[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[CH:13]=1)=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15183985HCID 15183985, compound

Product 1

HCID 58188126HCID 58188126, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of dimethyl 4′-methylbiphenyl-3,5-dicarboxylate (1.70 g, 5.98 mmol), MeOH (100 mL) and 2N aq. NaOH (8 mL) was stirred at 60° C. until LC-MS indicated the diester was almost completely consumed. After cooling, the mixture was concentrated in vacuo and acidified with 1N aq. HCl to pH<4 and extracted with EtOAc (100 mL×3). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated to yield a white solid (contained some dicarboxylic acid).

Workup

  1. customwas almost completely consumed
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated in vacuo
  4. extractionextracted with EtOAc (100 mL×3)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customto yield a white solid (

Sources & evidence

ORD record
ord-921f488c5fe34d2aa6d93223d1a89593
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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