Hydrochloric Acid → HCID 19777575, compound

HRID 1613007Notes

Reaction equation

HRID 1613007 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-59ac80adab004c0198e6b23fcc96b7c7
Source dataset
uspto-grants-1993_03
Patent number
US05191121

Reaction notes

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