Diethyl terephthalate → Terephthalic Acid

HRID 1378308Notes

Reaction equation

HRID 1378308 reaction equation
CC(CCO)CCC1C=CC=CC=1.CC[O:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([C:25]([O:27]CC)=[O:26])=[CH:21][CH:20]=1)=[O:18].C[O-].[Na+]>>[CH:20]1[C:19]([C:17]([OH:18])=[O:16])=[CH:24][CH:23]=[C:22]([C:25]([OH:27])=[O:26])[CH:21]=1

Participants

4

Reactant 3

HCID 12483Diethyl terephthalateHCID 1083123-Methyl-5-phenylpentan-1-olHCID 10942334Sodium Methoxide

Product 1

HCID 7489Terephthalic Acid

Conditions

Temperature
100 °C

Procedure

Phenoxanol in the amount of 35.80 g (0.201 mol) and diethyl p-phthalate in the amount of 13.00 g (0.067 mol) were combined in a 250 ml flask fitted with a heating mantel, take-off condenser, internal thermometer, and argon inlet. Sodium methoxide in the amount of 380 mg (6.70 mmol) was added to the contents of the flask. The mixture was heated to 100° C. for 5 h during which time it became very thick. The mixture was filtered with dichloromethane, concentrated by rotary evaporation, and stripped by Kugelrohr distillation to yield an oil. The oil was purified by column chromatography on silica gel eluting with a 2% solution of ethyl acetate in hexanes to yield a colorless oil that crystallized on standing. Purity of the product was determined by thin layer chromatography and the structure confirmed by 1H and 13C NMR.

Workup

  1. customfitted with a heating mantel, take-off condenser
  2. filtrationThe mixture was filtered with dichloromethane
  3. concentrationconcentrated by rotary evaporation
  4. distillationstripped by Kugelrohr distillation
  5. customto yield an oil
  6. customThe oil was purified by column chromatography on silica gel eluting with a 2% solution of ethyl acetate in hexanes
  7. customto yield a colorless oil that
  8. customcrystallized

Sources & evidence

ORD record
ord-7ec44a89d4f24171b400098fd4c61e41
Source dataset
uspto-grants-1997_09
Patent number
US05668102

Reaction notes

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