Ethyl Acrylate → HCID 11300104, compound

HRID 520738Notes

Reaction equation

HRID 520738 reaction equation
[C:1]1([C:7](=NN)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl([O-])=O.[Na+].C1(C(C2C=CC=CC=2)=[N+]=[N-])C=CC=CC=1.CCCCCC.[C:43]([O:47][CH2:48][CH3:49])(=[O:46])[CH:44]=[CH2:45]>C(Cl)Cl.O.[Cl-].C([N+](C)(C)CCCCCCCC)C1C=CC=CC=1>[CH2:48]([O:47][C:43]([CH:44]1[CH2:45][C:7]1([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:46])[CH3:49]

Participants

9

Reactant 5

HCID 8821Ethyl AcrylateHCID 14798Sodium HydroxideHCID 79304DiphenylmethylidenehydrazineHCID 23668197Sodium ChloriteHCID 88047892HCID 88047892, compound

Product 1

HCID 11300104HCID 11300104, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 13740Benzalkonium chloride C8 (BAC C8)Solvent

Procedure

Diphenylketone hydrazone (8.9 g, 45.4 mmol) in DCM (19 mL) was mixed with KI (0.45 g) in water (0.6 mL) and benzyldimethyloctylammonium chloride (10 mg). To the mixture was added the aqueous solution composing of 25% NaOH (27 mL), water (18 mL), and sodium chlorite (12-14%, 28 mL) at 5° C. with vigorous stirring. Twenty minutes later after addition, the stirring was turned off to let the reaction mixture separate. The red DCM solution was separated and dried over anhydrous Na2SO4. After removing the desiccant, the solvent was removed under reduced pressure; the residue was re-dissolved in hexane, and the unreacted hydrazone and side product was insoluble in hexane and removed by filtration. The red hexane diphenyl diazomethane solution was added to ethyl acrylate (13.6 g, 136 mmol) at 50° C. within 30 mints. When the red colour fade off the solvent and excess of ethyl acrylate was removed under reduced pressure to give crude product with 94% purity in 56-94% yield.

Workup

  1. additionTwenty minutes later after addition
  2. customseparate
  3. customThe red DCM solution was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. customAfter removing the desiccant
  6. customthe solvent was removed under reduced pressure
  7. dissolutionthe residue was re-dissolved in hexane
  8. customremoved by filtration
  9. customWhen the red colour fade off the solvent and excess of ethyl acrylate was removed under reduced pressure
  10. customto give crude product with 94% purity in 56-94% yield

Sources & evidence

ORD record
ord-6e9c1437c5bc437d990c387f659c0efb
Source dataset
uspto-grants-2016_05
Patent number
US09328074B2

Reaction notes

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