Water → Di-t-butyl terephthalate

HRID 53270

Reaction equation

HRID 53270 reaction equation
[C:1](Cl)(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[C:13]([OH:17])([CH3:16])([CH3:15])[CH3:14].[OH2:18]>N1C=CC=CC=1>[C:1]([O:11][C:2]([CH3:10])([CH3:3])[CH3:1])(=[O:18])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6386tert-ButanolHCID 7488Terephthaloyl chloride

Product 1

HCID 316007Di-t-butyl terephthalate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of terephthaloylchloride (2.00 g, 9.85 mmol) in dry pyridine (25.0 mL) was added tert-butyl alcohol (803 mg, 10.8 mmol). After 16 hours at 85° C. water (75.0 mL) was added and the solid filtered. The solid was dissolved in diethyl ether (40 mL) and washed with saturated sodium bicarbonate (2×75 mL). The organic phase was then dried over anhydrous magnesium sulfate and concentrated in vacuo to give 1.15 g (Y: 42%) of the title compound; 1H-NMR (CDCl3): δ8.01 (s, 4H), 1.60 (s, 18H).

Workup

  1. filtrationthe solid filtered
  2. dissolutionThe solid was dissolved in diethyl ether (40 mL)
  3. washwashed with saturated sodium bicarbonate (2×75 mL)
  4. dry with materialThe organic phase was then dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-295ebae9a55f4da2ba964b92e6fd5bff
Source dataset
uspto-grants-1997_04
Patent number
US05618839

Linked notes

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