Sodium Hydroxide → 4-Carbomethoxy-3-phenoxybenzoic acid

HRID 2121141Notes

Reaction equation

HRID 2121141 reaction equation
[O:1]([C:8]1[CH:17]=[C:16]([C:18]([O:20]C)=[O:19])[CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O>[C:10]([C:9]1[CH:14]=[CH:15][C:16]([C:18]([OH:20])=[O:19])=[CH:17][C:8]=1[O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([O:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23436153Dimethyl phenoxyterephthalate

Product 1

HCID 234362014-Carbomethoxy-3-phenoxybenzoic acidYield 66.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of dimethyl phenoxyterephthalate (10.4 g) in water. (50 mL) was added 50% aqueous NaOH (2.32 g) and water (4 mL) and the reaction mixture was stirred overnight at ambient temperature. The reaction mixture was concentrated in vacuo and the residue was partitioned between water and ether. The aqueous phase was acidified (a solid formed) and extracted with dichloromethane. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo to give 4-carbomethoxy-3-phenoxybenzoic acid (6.6 g) as a 68:32 mixture of hydrolysis isomers.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between water and ether
  3. customformed) and
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e723684f3af84d8480c7bd4102ac6921
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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