Terephthalic acid monomethylester chloride → Monomethyl terephthalate

HRID 1650903Notes

Reaction equation

HRID 1650903 reaction equation
[Cl-].[CH3:2][O:3][C:4](=[O:14])[C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1>N1C=CC=CC=1.C(OCC)(=O)C>[CH3:2][O:3][C:4](=[O:14])[C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 53442854Terephthalic acid monomethylester chloride

Product 1

HCID 15513Monomethyl terephthalateYield 45.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.07 g of the thus-obtained 4-tert.-butyl-2-hydroxyacetophenone in 10 ml of pyridine was added 1.125 g of terephthalic acid monomethylester chloride and the mixture stirred at room temperature for one night. The reaction mixture was diluted with ethyl acetate and washed with water, Cu(NO3) 0.2aq, water, aqueous solution of sodium hydrogencarbonate, and saturated saline solution, and then dried over MgSO4. The distillation of the solvent and purification by chromatography through silica gel column gave 900 mg of the derivative of terephthalic acid methylester (yield: 45.6%). The recrystallized product from methylenechloride-hexane has a m.p. of 95.5°-96° C.

Workup

  1. washwashed with water, Cu(NO3) 0.2aq, water, aqueous solution of sodium hydrogencarbonate, and saturated saline solution
  2. dry with materialdried over MgSO4
  3. distillationThe distillation of the solvent and purification by chromatography through silica gel column

Sources & evidence

ORD record
ord-649201eb144746d89d86f7c2ec070525
Source dataset
uspto-grants-1990_05
Patent number
US04925979

Reaction notes

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