Potassium Carbonate → HCID 86752381, compound

HRID 964889Notes

Reaction equation

HRID 964889 reaction equation
[C:1]([C:4]1[CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:7]([OH:14])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].Br[CH2:16][CH2:17][CH2:18][CH:19]=[CH2:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[I-].[K+]>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:14][CH2:20][CH2:19][CH2:18][CH:17]=[CH2:16])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 707041-Pentene, 5-bromo-2×HCID 85444Methyl 5-acetylsalicylate

Product 1

HCID 86752381HCID 86752381, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

Under dry condition, 3.58 g (18.41 mmol) of 5-acetylsalicylic acid, methyl ester is dissolved in 25 mL of dry N,N-dimethylformamide. To this solution is added 3.07 g (20.58 mmol) of 5-bromo-1-pentene, 6.83 (20.58 mmol) of potassium carbonate, and 0.246 g (1.65 mmol) of potassium iodide, and the reaction mixture is stirred for 24 hours at ambient temperature. Another portion of 5-bromopentene is added to the reaction, followed by one-half portions of the other two reagents above, and stirring is continued for 72 hours. The mixture is then evaporated under high vacuum at 70° C. The residue is partitioned between ether/water and the organic phase is separated, dried with magnesium sulfate, filtered, and evaporated under vacuum to leave 4.60 g (95%) of 5-acetyl-2-(4-pentenyloxy)benzoic acid, methyl ester as a yellow liquid: IR (neat) 1735, 1710, 1680 cm-1 ; 1HNMR (CDCl3) is consistent with the desired product; MS (FAB) m/e 263 (M+ +H). Analysis calculated for C15H18O4 : C, 68.69; H, 6.92; O, 24.40. Found: C, 68.60; H, 6.92; O, 24.46.

Workup

  1. stirringstirring
  2. waitis continued for 72 hours
  3. customThe mixture is then evaporated under high vacuum at 70° C
  4. customThe residue is partitioned between ether/water
  5. customthe organic phase is separated
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under vacuum

Sources & evidence

ORD record
ord-d4a2a89ca23d403a9c621eb6ee4050ab
Source dataset
uspto-grants-1998_06
Patent number
US05773001

Reaction notes

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