Potassium Iodide → HCID 18456920, compound

HRID 1272263Notes

Reaction equation

HRID 1272263 reaction equation
[OH:1][C:2]1[C:3]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([OH:12])[CH:6]=2.[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:16][O:15][C:13]([C:3]1[C:2]([OH:1])=[CH:11][C:10]2[C:5](=[CH:6][C:7]([O:12][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:8][CH:9]=2)[CH:4]=1)=[O:14]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 22173744HCID 22173744, compound

Product 1

HCID 18456920HCID 18456920, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of methyl 3,7-dihydroxy-2-naphthoate (2.2 g; 10 mmole), benzylchloride (Merck) (1.26 mL; 11.0 mmole), potassium iodide (1.8 g; 11.0 mmole) and potassium carbonate (2.0 g; 15 mmole) in acetone (30 mL) was refluxed for 7 hours and then cooled to room temperature. The inorganic precipitate was filtered off and washed with acetone, whereas the filtrate was evaporated to dryness The solid residue was dissolved in ethyl acetate and the resulting solution was washed with 1M hydrochloric acid. After drying with sodium sulfate the organic layer was evaporated and the dry residue was recrystallized from methanol, whereat 1.2 g (39%) of methyl-7-benzyloxy-3-hydroxy-2-naphthoate were obtained.

Workup

  1. temperaturewas refluxed for 7 hours
  2. filtrationThe inorganic precipitate was filtered off
  3. washwashed with acetone, whereas the filtrate
  4. customwas evaporated to dryness The solid residue
  5. dissolutionwas dissolved in ethyl acetate
  6. washthe resulting solution was washed with 1M hydrochloric acid
  7. dry with materialAfter drying with sodium sulfate the organic layer
  8. customwas evaporated
  9. customthe dry residue was recrystallized from methanol

Sources & evidence

ORD record
ord-50df2ebddcc440579b975c6ed055af89
Source dataset
uspto-grants-2007_04
Patent number
US07208518B2

Reaction notes

Loading…