1-Butanol → HCID 68486048, compound

HRID 2247084Notes

Reaction equation

HRID 2247084 reaction equation
OS(O)(=O)=O.O=S(=O)=O.[C:10]([OH:21])(=[O:20])[C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1.O1CC[CH2:25]OO1.[CH2:28](O)[CH2:29][CH2:30][CH3:31]>>[CH2:28]([O:16][C:15]([C:14]1[CH:18]=[C:19]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:21])[O:20][CH2:25]2)=[O:17])[CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 4

HCID 2631-ButanolHCID 7489Terephthalic AcidHCID 24681Fuming sulfuric acidHCID 19593658CID 19593658

Product 1

HCID 68486048HCID 68486048, compound

Conditions

Temperature
60 °C

Procedure

Oleum (25% SO3, 95 ml) is charged into a reactor (350 ml). Under stirring terephthalic acid (19.0 g; 0.11 mol) is added to the reactor and the mixture is heated to 60° C. After stirring for additional 40 min terephthalic acid (31.0 g; 0.19 mol) is added and the mixture is heated to 100° C. for 1 hour. The mixture is cooled to 25-30° C., trioxane (12.0 g; 0.13 mol) is added in portions and the reaction mixture is heated slowly to 120-125° C. and agitated at this temperature for 2 hours and for 4 hours at 145° C. The reaction mixture is cooled to 70° C. and added to a reactor containing butanol (350 ml) which has been heated to 65-70° C. over period of 45 min. The formed precipitates were diluted with butanol (150 ml) and stirring overnight at 40° C. The mixture was heated to reflux for 3 hours, cooled to 50-55° C. and water (500 ml) and heptane (500 ml) were added. The product was filtered off and dried.

Workup

  1. additionUnder stirring terephthalic acid (19.0 g; 0.11 mol) is added to the reactor
  2. additionis added
  3. temperaturethe mixture is heated to 100° C. for 1 hour
  4. temperatureThe mixture is cooled to 25-30° C.
  5. temperaturethe reaction mixture is heated slowly to 120-125° C.
  6. temperatureThe reaction mixture is cooled to 70° C.
  7. additionadded to a reactor
  8. temperaturehas been heated to 65-70° C. over period of 45 min
  9. customThe formed precipitates
  10. additionwere diluted with butanol (150 ml)
  11. stirringstirring overnight at 40° C
  12. temperatureThe mixture was heated
  13. temperatureto reflux for 3 hours
  14. temperaturecooled to 50-55° C.
  15. additionwater (500 ml) and heptane (500 ml) were added
  16. filtrationThe product was filtered off
  17. customdried

Sources & evidence

ORD record
ord-0dcadacd149b4b6385e72b1b255f7293
Source dataset
uspto-grants-2010_03
Patent number
US07687645B2

Reaction notes

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