1-Butanol → HCID 68486048, compound

HRID 2247083Notes

Reaction equation

HRID 2247083 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]>O.C1(C)C=CC=CC=1>[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

7

Reactant 4

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

Product 1

HCID 68486048HCID 68486048, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

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 30 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 130-135°C. and agitated at this temperature for 1 1/2 hours and for 4 hours at 155° C. The reaction mixture is cooled to 40° C. and over a period of 30 min added to a reactor containing butanol (300 ml) which has been heated to 95-100° C. Toluene (100 ml) and water (100 ml) was added to the formed suspension. The organic phase was separated and concentrated to dryness and redissolved in toluene (100 ml) and heptanes (100 ml) by heating at 75-80° C. The mixture was cooled to 25-30°C. for 30 min and 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 130-135°C.
  6. temperatureThe reaction mixture is cooled to 40° C. and over a period of 30 min
  7. additionadded to a reactor
  8. temperaturehas been heated to 95-100° C
  9. customThe organic phase was separated
  10. concentrationconcentrated to dryness
  11. dissolutionredissolved in toluene (100 ml)
  12. temperatureheptanes (100 ml) by heating at 75-80° C
  13. temperatureThe mixture was cooled to 25-30°C. for 30 min
  14. filtrationthe product was filtered off
  15. customdried

Sources & evidence

ORD record
ord-67c4b74b87e14d5999630d092fc9ebbe
Source dataset
uspto-grants-2010_03
Patent number
US07687645B2

Reaction notes

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