Hydrochloric Acid → HCID 19777575, compound

HRID 1885766Notes

Reaction equation

HRID 1885766 reaction equation
[H-].[Na+].[CH3:3][C:4](=[O:9])[C:5]([CH3:8])([CH3:7])[CH3:6].[C:10]([O:22]C)(=O)[C:11]1[CH:20]=[CH:19][CH:18]=[C:13]([C:14]([O:16]C)=O)[CH:12]=1.Cl>O1CCCC1>[CH3:6][C:5]([CH3:8])([CH3:7])[C:4](=[O:9])[CH2:3][C:14]([C:13]1[CH:18]=[CH:19][CH:20]=[C:11]([C:10](=[O:22])[CH2:3][C:4](=[O:9])[C:5]([CH3:8])([CH3:7])[CH3:6])[CH:12]=1)=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6416PinacoloneHCID 15088Dimethyl isophthalateHCID 24758Sodium hydride

Product 1

HCID 19777575HCID 19777575, compoundYield 61%

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 (15.5 mmol) of dimethyl isophthalate, and 30 ml of anhydrous tetrahydrofuran were mixed with stirring under nitrogen stream and refluxed with heating for 6 hours. After cooling the reaction mixture, 10 ml of 2N aqueous hydrochloric acid was added the product was extracted with chloroform. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated to give a crude product. Recrystallization using hexane afforded 3.1 gm of the target compound as colorless crystals (yield: 61%).

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 6 hours
  5. additionwas added the product
  6. extractionwas extracted with chloroform
  7. dry with materialThe extract was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated
  9. customto give a crude product
  10. customRecrystallization

Sources & evidence

ORD record
ord-bd6537f234c0419bb49687b8a5267acd
Source dataset
uspto-grants-1992_09
Patent number
US05146002

Reaction notes

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