Cyclopentadiene → endo-Dicyclopentadiene

HRID 531394

Reaction equation

HRID 531394 reaction equation
[C:1]1(=O)O[C:4](=O)[CH:3]=[CH:2]1.C1CC=CC=1.[CH2:13]1[CH:17]2C(C(O)=O)[CH:19](C(O)=O)[CH:14]1[CH:15]=[CH:16]2>O>[CH2:1]1[CH:19]2[C@@H:14]3[CH:13]=[CH:17][C@H:16]([CH:4]2[CH:3]=[CH:2]1)[CH2:15]3

Participants

5

Reactant 3

HCID 7612CyclopentadieneHCID 7923Maleic AnhydrideHCID 979655-Norbornene-2,3-dicarboxylic acid

Product 1

HCID 15618652endo-DicyclopentadieneYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Maleic anhydride (88.3 g, 0.90 mole) and water (150.0 g) was stirred at 20-30° C. under nitrogen, cyclopentadiene (30.0 g, 0.45 mole) was added dropwise over 1 hour and stirred at 25° C. for 6 hours, it was heated to 101° C. and held for 20 hours until 92% of nadic acid was converted to NBLCO2H as detected by GC. The wet crystal was filtered out and recrystallized from water to obtain 40.3 g of NBLCO2H with a yield of 49%.

Workup

  1. temperatureit was heated to 101° C.
  2. filtrationThe wet crystal was filtered out
  3. customrecrystallized from water
  4. customto obtain 40.3 g of NBLCO2H with a yield of 49%

Sources & evidence

ORD record
ord-ea0b2cfc69054a2e980fd4f688c47c69
Source dataset
uspto-grants-2016_05
Patent number
US09353213B2

Linked notes

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