Methyl 4-(3,4-dimethoxybenzyloxy)-3-chlorobenzoate → 4-(3,4-Dimethoxybenzyloxy)-3-chlorobenzoic acid

HRID 2099959Notes

Reaction equation

HRID 2099959 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][C:9]=1[Cl:18]>C1COCC1.CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[Cl:18]

Participants

5

Reactant 1

HCID 57796893Methyl 4-(3,4-dimethoxybenzyloxy)-3-chlorobenzoate

Product 1

HCID 577968974-(3,4-Dimethoxybenzyloxy)-3-chlorobenzoic acidYield 65%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1A (600 mg, 1.78 mmol) in THF (30 mL) and MeOH (10 mL) was treated with a solution of LiOH monohydrate (375 mg, 8.93 mmol) in water (10 mL) at room temperature. The resulting suspension was stirred at room temperature for 18 hours. The reaction was concentrated to 30 mL, diluted with water (50 mL) and cooled to 0° C. The solution was brought to pH 5 with 1 N HCl and the resulting solid was collected by vacuum filtration. Residual water was removed from the solid material using azeotrope with toluene to afford 1B as a white solid (370 mg, 65%).

Workup

  1. concentrationThe reaction was concentrated to 30 mL
  2. additiondiluted with water (50 mL)
  3. temperaturecooled to 0° C
  4. filtrationthe resulting solid was collected by vacuum filtration
  5. customResidual water was removed from the solid material

Sources & evidence

ORD record
ord-db42c4e011a34661a55b8388fa8a5fa3
Source dataset
uspto-grants-2009_08
Patent number
US07569725B2

Reaction notes

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