Ethylparaben → HCID 19043836, compound

HRID 1509792Notes

Reaction equation

HRID 1509792 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][CH:3]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH:20]=[CH2:21].C(=O)([O-])[O-].[K+].[K+].CN(C)C(=O)C>O>[CH:20]([O:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:11][CH:12]=1)=[CH2:21]

Participants

6

Reactant 4

HCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 54395919HCID 54395919, compound

Product 1

HCID 19043836HCID 19043836, compoundYield 128.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Ethyl p-hydroxybenzoate (33.2 g), 5-bromopentylvinyl ether (58.0 g), potassium carbonate (41.5 g) and N,N-dimethylacetamide (200 mL) were put into a 500-mL three-neck flask, and stirred at 120° C. for 5 hours. After cooled, the reaction mixture was poured into water (200 mL), extracted with ethyl acetate (500 mL), and washed two times with water (100 mL). This was dried with anhydrous magnesium sulfate, and filtered. The solvent was removed through concentration under reduced pressure, the residue was dissolved in methanol (100 mL), and a methanol solution (20 mL) of potassium hydroxide (16.8 g) was dropwise and gradually added thereto, and heated under reflux for 2 hours. After cooled, the formed crystal was collected through filtration and dissolved in water (1 L). Concentrated hydrochloric acid (25.7 mL) was added thereto, and the precipitated crystal was collected through filtration under reduced pressure, and washed with water. This was dried to give 4-(5-vinyloxypentyloxy)benzoic acid (TP-29C) (64.3 g, 90%). Production of 2,3,6,7,10,11-hexa(4-(5-vinyloxypentyloxy)benzoyloxy)triphenylene (TP-29):

Workup

  1. temperatureAfter cooled
  2. extractionextracted with ethyl acetate (500 mL)
  3. washwashed two times with water (100 mL)
  4. dry with materialThis was dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed through concentration under reduced pressure
  7. dissolutionthe residue was dissolved in methanol (100 mL)
  8. additiongradually added
  9. temperatureheated
  10. temperatureunder reflux for 2 hours
  11. temperatureAfter cooled
  12. filtrationthe formed crystal was collected through filtration
  13. dissolutiondissolved in water (1 L)
  14. additionConcentrated hydrochloric acid (25.7 mL) was added
  15. filtrationthe precipitated crystal was collected through filtration under reduced pressure
  16. washwashed with water
  17. customThis was dried

Sources & evidence

ORD record
ord-bbbff25e811c444388c682c4814b6bad
Source dataset
uspto-grants-2012_07
Patent number
US08211598B2

Reaction notes

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