Terephthaloyl chloride → Monomethyl terephthalate

HRID 346472Notes

Reaction equation

HRID 346472 reaction equation
C(Cl)(=O)C1C=CC(C(Cl)=O)=CC=1.[CH3:13][O:14][C:15](=[O:26])[C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=1.O[Li].O>ClCCl.CO>[CH3:13][O:14][C:15](=[O:26])[C:16]1[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7488Terephthaloyl chlorideHCID 8441Dimethyl terephthalateHCID 168937Lithium hydroxide, monohydrate

Product 1

HCID 15513Monomethyl terephthalate

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 20.3 g (100 mmol) terephthaloyl chloride in 100 ml dichloromethane was added to 100 ml anhydrous methanol at 0° C. The reaction was left 1.5 h at rt. The reaction mixture was evaporated and the residue was dissolved dichloromethane. The organic phase was washed with saturated NaHCO3 aq. The organic phase was dried and evaporated. Yield 18.3 g (94.2 mmol, 94%). A solution of 18.3 g (94.2 mmol) of terephthalic acid dimethyl ester and 3.96 g (94.2 mmol) LiOH.H2O in anhydrous methanol (did not dissolve completely) was stirred for 5 d at rt. The solvent was evaporated and the product was dissolved in water. The aqueous phase was washed with dichloromethane. The aqueous phase was made acidic with 2 M HCl aq. The product precipitated from the aqueous phase. The product was filtered off and dried in vacuo. The product was dissolved in 1 L dry ethanol, and thereafter 4 l water was added slowly while stirring. The product precipitated slowly overnight at +4°C. The product was filtered and dried in vacuo. Yield 8.61 g (48 mmol, 51%)

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue was dissolved dichloromethane
  3. washThe organic phase was washed with saturated NaHCO3 aq. The organic phase
  4. customwas dried
  5. customevaporated
  6. customThe solvent was evaporated
  7. dissolutionthe product was dissolved in water
  8. washThe aqueous phase was washed with dichloromethane
  9. customprecipitated from the aqueous phase
  10. filtrationThe product was filtered off
  11. customdried in vacuo
  12. dissolutionThe product was dissolved in 1 L dry ethanol
  13. addition4 l water was added slowly
  14. stirringwhile stirring
  15. customThe product precipitated slowly overnight at +4°C
  16. filtrationThe product was filtered
  17. customdried in vacuo

Sources & evidence

ORD record
ord-8d2c561d789b4c1093ae25f891804fb3
Source dataset
uspto-grants-2007_02
Patent number
US07173024B2

Reaction notes

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