Potassium Iodide → HCID 18402120, compound

HRID 1018767Notes

Reaction equation

HRID 1018767 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([OH:12])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].Br[CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH3:16][CH2:15][CH:14]([O:1][C:2]1[CH:3]=[C:4]([OH:12])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7])[CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 157383-BromopentaneHCID 16523Methyl 2,4-Dihydroxybenzoate

Product 1

HCID 18402120HCID 18402120, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The methyl 4-[pent-3-oxy]salicylate used was prepared as follows. A mixture of methyl 4-hydroxysalicylate (74 g, 0.44 mole), 3-bromopentane (80 g, 0.53 mole), potassium iodide (20 g) and potassium carbonate (100 g) in methyl ethyl ketone (MEK, 500 mL) was heated at reflux for 65 hours. The cooled reaction mixture was then filtered and concentrated under reduced pressure. The resultant oily residue was stirred with dilute hydrochloric acid, then extracted into dichloromethane. The dichloromethane solution was washed with brine, dried over anhydrous sodium sulfate and concentrated to a clear liquid (67.0 g, 64% yield). The structure of this compound was confirmed by mass spectroscopy and by 1H and 13C NMR spectroscopy.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 65 hours
  3. customThe cooled reaction mixture
  4. filtrationwas then filtered
  5. concentrationconcentrated under reduced pressure
  6. extractionextracted into dichloromethane
  7. washThe dichloromethane solution was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-552418eddac64fc59506c099f7d2b808
Source dataset
uspto-grants-2002_11
Patent number
US06482950B1

Reaction notes

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