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

HRID 875386

Reaction equation

HRID 875386 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-ab3a71d21de342cca5cba42610df5003
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Linked notes

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