Potassium Iodide → HCID 57864373, compound

HRID 1672648Notes

Reaction equation

HRID 1672648 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:13]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[C:13]([C:17]1[CH:18]=[CH:19][C:20]([CH2:21][O:12][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:11][C:6]=2[C:7]([O:9][CH3:10])=[O:8])=[CH:23][CH:24]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 88198Benzene, 1-(chloromethyl)-4-(1,1-dimethylethyl)-HCID 2783186Methyl 5-fluoro-2-hydroxybenzoate

Product 1

HCID 57864373HCID 57864373, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4.44 g (26 mmol) of methyl 5-fluoro-2-hydroxybenzoate [CAS 391-92-4], 5.25 g 28.7 mmol) of 4-tert-butylbenzyl chloride [CAS 19692-45-6], 18.0 g (130 mmol) of potassium carbonate and 6.5 g (39.2 mmol) of potassium iodide are dissolved in 25 ml of acetone and stirred under reflux for 12 h. The solvent is distilled out in vacuo, and the residue is taken up in ethyl acetate and washed once with 10% strength sodium hydroxide solution and three times with 1 N hydrochloric acid. The solution is dried over sodium sulfate, filtered, washed with ethyl acetate and concentrated. 8.36 g (26 mmol, 100% of theory) of the title compound are isolated.

Workup

  1. temperatureunder reflux for 12 h
  2. distillationThe solvent is distilled out in vacuo
  3. washwashed once with 10% strength sodium hydroxide solution and three times with 1 N hydrochloric acid
  4. dry with materialThe solution is dried over sodium sulfate
  5. filtrationfiltered
  6. washwashed with ethyl acetate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7f2f652ffbba4b65ae8ac04fbe0ad739
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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