HCID 66906348, compound → HCID 66906150, compound

HRID 1915143Notes

Reaction equation

HRID 1915143 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[C:5](=[C:10]([O:14][CH2:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7]>[OH-].[Na+]>[Cl:22][C:20]1[CH:21]=[C:16]([CH:17]=[C:18]([Cl:23])[CH:19]=1)[CH2:15][O:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:4]([C:3]([OH:24])=[O:2])[C:5]=1[C:6]([OH:8])=[O:7]

Participants

3

Reactant 1

HCID 66906348HCID 66906348, compound

Product 1

HCID 66906150HCID 66906150, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-(3,5-dichloro-benzyloxy)-phthalic acid dimethyl ester (0.42 g, 1.2 mmol) in reagent alcohol (10 mL) and 3 N sodium hydroxide (10 mL) was refluxed for two hours. The solution was evaporated and the residue was dissolved in water (10 mL) and washed with methylene chloride (2×10 mL) then acidified to pH around 4. The resulting mixture was extracted with ethyl acetate (2×10 mL) and the combined organic layers was washed with water (2×10 mL), dried and concentrated to give 3-(3,5-dichloro-benzyloxy)-phthalic acid as an off-white solid (0.34 g, 88% yield). The product was used in the next step without further purification.

Workup

  1. customThe solution was evaporated
  2. dissolutionthe residue was dissolved in water (10 mL)
  3. washwashed with methylene chloride (2×10 mL)
  4. extractionThe resulting mixture was extracted with ethyl acetate (2×10 mL)
  5. washthe combined organic layers was washed with water (2×10 mL)
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3d1defa023674524ae3d7865d603555d
Source dataset
uspto-grants-2013_12
Patent number
US08614328B2

Reaction notes

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