Sodium Hydroxide → HCID 12247210, compound

HRID 650922Notes

Reaction equation

HRID 650922 reaction equation
C[O:2][C:3]([C:5]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])=[C:9]([O:19][CH3:20])[CH:8]=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+]>C(O)C>[CH3:20][O:19][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 282428methyl 2',6-dimethoxybiphenyl-2-carboxylate

Product 1

HCID 12247210HCID 12247210, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 188.4 mg (0.69 mmol) of ester prepared in Step A and 0.28 mL (1.39 mmol) of 5N NaOH in 2 mL of ethanol was refluxed under nitrogen for 1.5 hours. The mixture was partitioned between EtOAc, ice, 2N HCl, and the organic phase was separated, washed with brine, dried over Na2SO4, filtered, evaporated, and dried in vacuo to give 171.6 mg of the title acid which was used without further purification.

Workup

  1. temperaturewas refluxed under nitrogen for 1.5 hours
  2. customThe mixture was partitioned between EtOAc, ice, 2N HCl
  3. customthe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customdried in vacuo

Sources & evidence

ORD record
ord-73b0e22977914b6f9ac0cb0874aae425
Source dataset
uspto-grants-2001_08
Patent number
US06277843B1

Reaction notes

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