3-(5-Chloro-thiophen-2-ylmethoxy)-phthalic acid dimethyl ester → 3-(5-Chloro-thiophen-2-ylmethoxy)-phthalic acid

HRID 709582Notes

Reaction equation

HRID 709582 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[C:5](=[C:10]([O:14][CH2:15][C:16]2[S:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7]>[OH-].[Na+]>[Cl:21][C:18]1[S:17][C:16]([CH2:15][O:14][C:10]2[CH:11]=[CH:12][CH:13]=[C:4]([C:3]([OH:22])=[O:2])[C:5]=2[C:6]([OH:8])=[O:7])=[CH:20][CH:19]=1

Participants

3

Reactant 1

HCID 669061873-(5-Chloro-thiophen-2-ylmethoxy)-phthalic acid dimethyl ester

Product 1

HCID 669067303-(5-Chloro-thiophen-2-ylmethoxy)-phthalic acidYield 76.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-(5-chloro-thiophen-2-ylmethoxy)-phthalic acid dimethyl ester (2.3 g, 6.7 mmol) in reagent alcohol (100 mL) and 3 N sodium hydroxide (60 mL) was refluxed for two hours. The solution was evaporated and the residue was dissolved in water (100 mL) and washed with methylene chloride (3×100 mL) then acidified to pH around 4. The resulting mixture was extracted with ethyl acetate (2×100 mL) and the combined organic layers was washed with water (2×100 mL), dried and concentrated to give 3-(5-chloro-thiophen-2-ylmethoxy)-phthalic acid as an off-white solid (1.6 g, 76% 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 (100 mL)
  3. washwashed with methylene chloride (3×100 mL)
  4. extractionThe resulting mixture was extracted with ethyl acetate (2×100 mL)
  5. washthe combined organic layers was washed with water (2×100 mL)
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cdc9fc637b2044c38c9e9948b5de3b82
Source dataset
uspto-grants-2015_11
Patent number
US09181216B2

Reaction notes

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