Potassium Iodide → HCID 10780025, compound

HRID 322920Notes

Reaction equation

HRID 322920 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1>CC(C)=O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH2:26][C:25]2[CH:28]=[CH:29][C:22]([Cl:21])=[CH:23][CH:24]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 16523Methyl 2,4-Dihydroxybenzoate

Product 1

HCID 10780025HCID 10780025, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 180AcetoneSolvent

Procedure

A solution of methyl 2,4-dihydroxybenzoate (6.73 g) in acetone (250 mL) is treated with potassium iodide (2.66 g), tetrabutylammonium chloride (0.05 g), potassium carbonate (5.53 g), and 4-chlorobenzyl chloride (7.08 g), and stirred at reflux for 24 hours. The mixture is filtered, and the filtrate evaporated. The residue is taken up in ethyl acetate, washed with water, dried, and evaporated. The residue is recrystallized from ethyl acetate to yield methyl 2-hydroxy-4-(4-chlorobenzyloxy)benzoate as colourless crystals (5.3 g, 45%), m.p. 119-121° C. 1H NMR (DMSO) 3.9(3H,s), 5.2(2H,s), 6.6(2H,m), 7.5(4H,m), 7.7(1H,d).

Workup

  1. temperatureat reflux for 24 hours
  2. filtrationThe mixture is filtered
  3. customthe filtrate evaporated
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a3716295087f4d6785155ca26be707ff
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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