Acrylic Acid → HCID 86743376, compound

HRID 1607791Notes

Reaction equation

HRID 1607791 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[C:6]([O:10][CH3:11])(=[O:9])[CH:7]=[CH2:8].[CH2:12]=[CH:13][CH2:14][CH2:15][CH:16]=[CH2:17]>CCCCCC>[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[C:6]([O:10][CH3:11])(=[O:9])[CH:7]=[CH2:8].[CH2:12]=[CH:13][CH2:14][CH2:15][CH:16]=[CH2:17]

Participants

5

Reactant 3

HCID 6581Acrylic AcidHCID 7294Methyl AcrylateHCID 115981,5-Hexadiene2×

Product 1

HCID 86743376HCID 86743376, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Into a 500 ml, three necked round-bottom flask equipped with a cold-finger,addition funnel, and mechanical stirrer were charged approximately 230 ml of hexane, 32.35 ml of acrylic acid, and 5 ml of methyl acrylate. The flask was placed in a water bath at 25° C. and purged with nitrogenfor 45 minutes. Next, 1.26 ml of 1,5-hexadiene (HD) was placed in an addition funnel and diluted to 60 ml with hexane which had been stored under nitrogen. The water bath temperature was raised to reflux temperature (65°-70° C.) and 6 ml (10%) of the HD solution was added to the reaction mixture. The reaction was initiated with 1.0 weight % benzoyl peroxide which had been dissolved in 50 ml of hexane. After a white precipitate began forming (about 5 minutes), the remaining HD solution was added incrementally over a 1-hour period. After addition of the HD solution was complete, the reaction was allowed to proceed for 30 minutes. Product was filtered, washed with hexane, dried under vacuum, and ground into a fine white powder.

Workup

  1. customInto a 500 ml, three necked round-bottom flask equipped with a cold-finger,addition funnel, and mechanical stirrer
  2. customThe flask was placed in a water bath at 25° C.
  3. custompurged with nitrogenfor 45 minutes
  4. customNext, 1.26 ml of 1,5-hexadiene (HD) was placed in an addition funnel
  5. additiondiluted to 60 ml with hexane which
  6. temperatureThe water bath temperature was raised
  7. temperatureto reflux temperature (65°-70° C.) and 6 ml (10%) of the HD solution
  8. additionwas added to the reaction mixture
  9. dissolutionhad been dissolved in 50 ml of hexane
  10. customAfter a white precipitate began forming (about 5 minutes)
  11. filtrationProduct was filtered
  12. washwashed with hexane
  13. customdried under vacuum, and ground into a fine white powder

Sources & evidence

ORD record
ord-8dab3d0a2faa499b83a1e658b3ea51c2
Source dataset
uspto-grants-1989_09
Patent number
US04867896

Reaction notes

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