Hydrochloric Acid → HCID 19777569, compound

HRID 1613008Notes

Reaction equation

HRID 1613008 reaction equation
[H-].[Na+].[CH3:3][C:4](=[O:9])[C:5]([CH3:8])([CH3:7])[CH3:6].[CH3:10][O:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=O)=[CH:14][C:13]=1[C:22]([O:24]C)=O.Cl>O1CCCC1>[CH3:10][O:11][C:12]1[CH:21]=[CH:20][C:15]([C:16](=[O:18])[CH2:3][C:4](=[O:9])[C:5]([CH3:8])([CH3:7])[CH3:6])=[CH:14][C:13]=1[C:22](=[O:24])[CH2:3][C:4](=[O:9])[C:5]([CH3:8])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6416PinacoloneHCID 24758Sodium hydrideHCID 89938Dimethyl 4-methoxyisophthalate

Product 1

HCID 19777569HCID 19777569, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 100 ml three-necked flask equipped with a mechanical stirrer, dropping funnel, reflux condenser, and a nitogen-inlet tube, 1.5 gm (38 mmol) of 60% sodium hydride, 3.6 gm (36 mmol) of pinacolone, 3.0 gm (13.4 mmol) of dimethyl 4-methoxyisophthalate, and 30 ml of anhydrous tetrahydrofuran were mixed with stirring under nitrogen stream and refluxed with heating for 5 hours. After cooling the reaction mixture, 10 ml of 2N aqueous hydrochloric acid was added, and the product was extracted with chloroform. The extract was dried over anhydrous sodium sulfate and the solvent was removed by evaporation. The crude product was recrystallized using hexane to obtain 3.2 gm of the target compound as colorless crystals (yield: 66%).

Workup

  1. customIn a 100 ml three-necked flask equipped with a mechanical stirrer
  2. temperaturereflux condenser, and a nitogen-inlet tube
  3. temperaturerefluxed
  4. temperaturewith heating for 5 hours
  5. additionwas added
  6. extractionthe product was extracted with chloroform
  7. dry with materialThe extract was dried over anhydrous sodium sulfate
  8. customthe solvent was removed by evaporation
  9. customThe crude product was recrystallized

Sources & evidence

ORD record
ord-9ccb1551636e4d23ae007cf3aa514928
Source dataset
uspto-grants-1993_03
Patent number
US05191121

Reaction notes

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