Hydrochloric Acid → HCID 19777571, compound

HRID 1613012Notes

Reaction equation

HRID 1613012 reaction equation
C(OC([O:6][C:7]([CH3:12])([CH3:11])[C:8](=[O:10])[CH3:9])C)C.[H-].[Na+].CO[C:17](=[O:28])[C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=O)=[CH:20][CH:19]=1.Cl>O1CCCC1>[OH:6][C:7]([CH3:12])([CH3:11])[C:8](=[O:10])[CH2:9][C:22]([C:21]1[CH:20]=[CH:19][C:18]([C:17](=[O:28])[CH2:9][C:8](=[O:10])[C:7]([CH3:11])([OH:6])[CH3:12])=[CH:27][CH:26]=1)=[O:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8441Dimethyl terephthalateHCID 24758Sodium hydrideHCID 197775643-(1-Ethoxyethoxy)-3-methyl-butane-2-one

Product 1

HCID 19777571HCID 19777571, compoundYield 49%

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, 9.9 gm (57 mmol) of above-mentioned 3-(1-ethoxyethoxy)-3-methyl-butane-2-one, 2.3 gm (57 mmol) of 60% sodium hydride, 5.0 gm (25 mmol) of dimethylterephthalate and 50 ml of anhydrous tetrahydrofuran were mixed with stirring under nitrogen stream, and the refluxing under heat was continued for 7 hours. After cooling the reaction mixture, 30 ml of 2N hydrochloric acid was added and the mixture was extracted with chloroform. The extract was dried over anhydrous sodium sulfate and the solvent was removed by evaporation. The reaction mixture was stirred at room temperature while adding 30 ml of methnol with ten drops of 2N hydrochloric acid. A mixed solvent of acetone-chloroform was added to the crude product, and recrystallization afforded 4.1 gm of the title compound as pale yellow crystals (yield: 48%).

Workup

  1. customIn a 100 ml three-necked flask equipped with a mechanical stirrer
  2. temperaturereflux condenser, and a nitogen-inlet tube
  3. temperaturethe refluxing under heat
  4. additionwas added
  5. extractionthe mixture was extracted with chloroform
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. customthe solvent was removed by evaporation
  8. stirringThe reaction mixture was stirred at room temperature
  9. additionwhile adding 30 ml of methnol with ten drops of 2N hydrochloric acid
  10. additionA mixed solvent of acetone-chloroform was added to the crude product, and recrystallization

Sources & evidence

ORD record
ord-594f2baa9abc408b8d87430b8ce6a867
Source dataset
uspto-grants-1993_03
Patent number
US05191121

Reaction notes

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