1,4-Butanediol → 3,8-Dioxabicyclo[8.2.2]tetradeca-1(12),10,13-triene-2,9-dione

HRID 434115Notes

Reaction equation

HRID 434115 reaction equation
[C:1]([O:13][CH3:14])(=[O:12])[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH2:15](O)[CH2:16]CCO>>[C:6]1(=[O:7])[O:8][CH2:9][CH2:16][CH2:15][CH2:14][O:13][C:1](=[O:12])[C:2]2[CH:11]=[CH:10][C:5]1=[CH:4][CH:3]=2

Participants

3

Reactant 2

HCID 80641,4-ButanediolHCID 8441Dimethyl terephthalate

Product 1

HCID 216575113,8-Dioxabicyclo[8.2.2]tetradeca-1(12),10,13-triene-2,9-dione

Conditions

Temperature
160 °C

Procedure

474 g of dimethyl terephthalate and 660 g of 1,4-butanediol were placed into a 2 liter round bottomed flack fitted with a condenser, vigreux distillation column, nitrogen inlet and mechanical stirrer. The reactor was placed inside an isomantle and slowly heated to a temperature of 160° C. At this point 248 mg of tetrabutyl titanate catalyst pre-mixed with a small amount of pure 1,4-butanediol was injected, whilst the reactor contents were being stirred. The reaction was allowed to continue for 1 hour at 200° C. Methanol vapor which is produced during the reaction, was removed via the vigreux distillation column and combined condenser. The composition of the product was 82% by weight of butylene terephthalate (as confirmed by NMR) and 18% by weight of 1,4-butanediol.

Workup

  1. customfitted with a condenser
  2. distillationvigreux distillation column, nitrogen inlet and mechanical stirrer
  3. additionAt this point 248 mg of tetrabutyl titanate catalyst pre-mixed with a small amount of pure 1,4-butanediol
  4. customMethanol vapor which is produced during the reaction
  5. customwas removed via the vigreux distillation column

Sources & evidence

ORD record
ord-58d1e74490a04bfeb2e3740d01fafaf4
Source dataset
uspto-grants-2003_12
Patent number
US06670429B2

Reaction notes

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