Hydrochloric Acid → HCID 19777565, compound

HRID 1613006Notes

Reaction equation

HRID 1613006 reaction equation
[H-].[Na+].[CH3:3][C:4](=[O:9])[C:5]([CH3:8])([CH3:7])[CH3:6].CO[C:12](=[O:23])[C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=O)=[CH:15][CH:14]=1.Cl>O1CCCC1>[CH3:6][C:5]([CH3:8])([CH3:7])[C:4](=[O:9])[CH2:3][C:17]([C:16]1[CH:15]=[CH:14][C:13]([C:12](=[O:23])[CH2:3][C:4](=[O:9])[C:5]([CH3:8])([CH3:7])[CH3:6])=[CH:22][CH:21]=1)=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6416PinacoloneHCID 8441Dimethyl terephthalateHCID 24758Sodium hydride

Product 1

HCID 19777565HCID 19777565, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a 2 1 four-necked flask equipped with a mechanical stirrer, dropping funnel, thermometer, reflux condenser, and a nitrogen-inlet tube, 32 gm (0.8 mol) of 60% sodium hydride, 79 gm (0.79 mol) of pinacolone, and 700 ml of anhydrous tetrahydrofuran were mixed with stirring under nitrogen stream. To this solution, 70 gm (0.36 mol) of dimethylterephthalate in 300 ml of tetrahydrofuran was added dropwise over one hour. After the addition, the reaction mixture was refluxed with heating for 6 hours, and was cooled to room temperature. After addition of 180 ml of 2N aqueous hydrochloric acid, the reaction mixture was extracted with chloroform. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated to give a crude product. The crude product was recrystallized using hexane to obtain 78 gm of the target compound as colorless scales (yield: 66%).

Workup

  1. customIn a 2 1 four-necked flask equipped with a mechanical stirrer
  2. temperaturethermometer, reflux condenser, and a nitrogen-inlet tube
  3. additionAfter the addition
  4. temperaturethe reaction mixture was refluxed
  5. temperaturewith heating for 6 hours
  6. extractionthe reaction mixture was 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. customThe crude product was recrystallized

Sources & evidence

ORD record
ord-53d6830e10cb416987e77f2d4da41d98
Source dataset
uspto-grants-1993_03
Patent number
US05191121

Reaction notes

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