Maleic Anhydride → HCID 53683387, compound

HRID 1386570Notes

Reaction equation

HRID 1386570 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH3:8]/[CH:9]=[C:10](/[CH:12]=[CH:13]/[CH:14]=[C:15]([CH3:17])[CH3:16])\[CH3:11]>>[CH3:11][C:10]1[CH2:12][CH:13]([CH:14]=[C:15]([CH3:17])[CH3:16])[CH:3]2[C:4](=[O:5])[O:6][C:1](=[O:7])[CH:2]2[C:9]=1[CH3:8]

Participants

3

Reactant 2

HCID 7923Maleic Anhydride3×HCID 53688212,4,6-Octatriene, 2,6-dimethyl-, (4E,6E)-2×

Product 1

HCID 53683387HCID 53683387, compound

Conditions

Temperature
50 °C

Procedure

Maleic anhydride (39.88 g), 0.407 mol) and allo-ocimene (55.34 g, 0.407 mol) were charged in a 250 ml three necked round-bottom flask, connected with a reflux condenser. Immediately after addition of the maleic anhydride to the allo-ocimene, the mixture turned intense orange/yellow. The mixture was warmed carefully to 50° C. Then, as the maleic anhydride started to melt, a violent and exothermic Diels-Alder reaction took place. The temperature rose rapidly to 170-190° C. while the color of the mixture became less intense. After about 10 minutes the temperature started to drop. The mixture was kept at 100° C. for one hour. 93.71 g (0.401 mol=98.4%) of a yellow product was obtained that solidified on standing (melting point 78-82° C.). The product was washed with pentane in order to remove the yellow color to a great extent. The yield dropped during washing to about 65%. The anhydride was recrystallized from heptane to yield a white solid (melting point 83.5° C.-84° C.). Yield after recrystallization was 60%).

Workup

  1. customconnected with a reflux condenser
  2. customa violent and exothermic Diels-Alder reaction
  3. customrose rapidly to 170-190° C. while the color of the mixture
  4. waitThe mixture was kept at 100° C. for one hour
  5. custom93.71 g (0.401 mol=98.4%) of a yellow product was obtained that solidified
  6. washThe product was washed with pentane in order
  7. customto remove the yellow color to a great extent
  8. additionThe yield dropped
  9. washduring washing to about 65%
  10. customThe anhydride was recrystallized from heptane

Sources & evidence

ORD record
ord-db8411aa17684f80803d675356a762f3
Source dataset
uspto-grants-2001_07
Patent number
US06265531B1

Reaction notes

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