Hydrochloric Acid → HCID 82112865, compound

HRID 628509Notes

Reaction equation

HRID 628509 reaction equation
[O:1]1CC[CH2:3][CH2:2]1.[H-].[Na+].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][C:11]=1[CH3:19].Cl>C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1.O.C(O)C.C(OCC)(=O)C>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH2:17][C:2](=[O:1])[CH3:3])=[CH:12][C:11]=1[CH3:19]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 248061-(4-Methoxy-3-methylphenyl)ethan-1-one

Product 1

HCID 82112865HCID 82112865, compound

Reagents, catalysts & solvents 4

HCID 26541Dibenzo-18-crown-6CatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

At room temperature, to tetrahydrofuran 50 ml was added 55% sodium hydride 3.07 g and ethyl acetate 5.90 g and the resulting mixture was stirred for a half hour. Then, thereto was added 1 (4 methoxy-3-methylphenyl)-ethanone (described in Reference Preparation example 48) 5.50 g, dibenzo-18-crown-6 0.024 g and ethanol 1 ml and the resulting mixture was stirred with heating under reflux for six hours. To the reaction mixture was added water and the resulting mixture was acidified with aqueous 10% hydrochloric acid solution and was extracted with ethyl acetate. The organic layer was washed with water and was dried over anhydrous magnesium sulfate, and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(4-methoxy-3-methyl-phenyl)-butane-1,3-dione 6.50 g.

Workup

  1. stirringthe resulting mixture was stirred
  2. temperaturewith heating
  3. temperatureunder reflux for six hours
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-749fad6529434d6d91c7a2230e0a1966
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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