Benzoic acid, 4-(acetyloxy)- → HCID 19365282, compound

HRID 850820Notes

Reaction equation

HRID 850820 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].S(Cl)(Cl)=O>>[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:11][CH2:12][CH2:13][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 16865Benzoic acid, 4-(acetyloxy)-HCID 24386Thionyl Chloride

Product 1

HCID 19365282HCID 19365282, compound

Procedure

3.5 Grams of 4-acetoxybenzoic acid was added to 25 ml of thionyl chloride, and the mixture was allowed to react under reflux for 10 hours. Then, excessive thionyl chloride was distilled off, 10 ml of pyridine and 50 ml of toluene were then added, and 1.5 g of n-heptanol was dropwise added. After the addition, the mixture was refluxed under heat for 4 hours, and then the reaction mixture was allowed to cool and diluted with 500 ml of dichloromethane. An organic layer was consecutively washed with diluted hydrochloric acid, with a 1N sodium hydroxide aqueous solution and with water, and dried over magnesium sulfate. Further, the solvent was distilled off to give 1.7 g of the crude intended product.

Workup

  1. customto react
  2. temperatureunder reflux for 10 hours
  3. distillationThen, excessive thionyl chloride was distilled off
  4. addition10 ml of pyridine and 50 ml of toluene were then added
  5. addition1.5 g of n-heptanol was dropwise added
  6. additionAfter the addition
  7. temperaturethe mixture was refluxed
  8. temperatureunder heat for 4 hours
  9. temperatureto cool
  10. additiondiluted with 500 ml of dichloromethane
  11. washAn organic layer was consecutively washed with diluted hydrochloric acid, with a 1N sodium hydroxide aqueous solution and with water
  12. dry with materialdried over magnesium sulfate
  13. distillationFurther, the solvent was distilled off
  14. customto give 1.7 g of the crude

Sources & evidence

ORD record
ord-9a98a47f0a764d6f8e7032bf1efeaa6f
Source dataset
uspto-grants-2000_01
Patent number
US06018070

Reaction notes

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