Sodium Hydroxide → 4-(2-Methoxyphenyl)-3-methylbenzoic acid

HRID 1950815Notes

Reaction equation

HRID 1950815 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([O:19]C)=[O:18])=[CH:13][C:12]=1[CH3:21]>CCO>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][C:12]=1[CH3:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67528780Methyl 2'-methoxy-2-methylbiphenyl-4-carboxylate

Product 1

HCID 219477594-(2-Methoxyphenyl)-3-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydroxide (5M; 4.7 mL; 23.4 mmol; 3 eq.) was added to a solution of methyl 2′-methoxy-2-methylbiphenyl-4-carboxylate (2 g; 7.8 mmol; 1 eq.) in EtOH (60 mL) and the reaction mixture was stirred at 60° C. for one hour then concentrated in vacuo. The residue was taken up in water (400 mL) and washed with ethyl acetate (2×200 mL) then acidified to pH 2 with conc. HCl. The solution was concentrated to ca. 80 mL, the precipitate filtered off and dried to afford the title compound as a brown solid.

Workup

  1. concentrationthen concentrated in vacuo
  2. washwashed with ethyl acetate (2×200 mL)
  3. concentrationThe solution was concentrated to ca. 80 mL
  4. filtrationthe precipitate filtered off
  5. customdried

Sources & evidence

ORD record
ord-497fe0ca0603455088a35642226d4428
Source dataset
uspto-grants-2013_03
Patent number
US08404676B2

Reaction notes

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