Sodium Hydroxide → 1-Methyl 2,6-dichloro-1,4-benzenedicarboxylate

HRID 2201779Notes

Reaction equation

HRID 2201779 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[C:13]([O:15][CH3:16])=[O:14].[OH-].[Na+]>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([Cl:12])[C:3]=1[C:13]([O:15][CH3:16])=[O:14])[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 7730227Dimethyl 2,6-dichloroterephthalate

Product 1

HCID 186730161-Methyl 2,6-dichloro-1,4-benzenedicarboxylateYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the stirred solution of dimethyl 2,6-dichlorobenzene-1,4-dicarboxylate (2 g, 7.6 mmol, Step b) in tetrahydrofuran and water (1:1, 20 mL), sodium hydroxide (304 mg, 7.6 mmol) was added and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under vacuum and the residue was neutralized using cold hydrochloric acid (1N). The precipitated solid was filtered under suction, washed with hexane and dried to afford 3,5-dichloro-4-(methoxycarbonyl)benzoic acid as an white solid (1.5 g, 85%).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. filtrationThe precipitated solid was filtered under suction
  3. washwashed with hexane
  4. customdried

Sources & evidence

ORD record
ord-1bbdb042830f4a4783b3709f293ea600
Source dataset
uspto-grants-2016_06
Patent number
US09364466B2

Reaction notes

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