Toluene → 5-Norbornene-2-carboxylic acid

HRID 1748916Notes

Reaction equation

HRID 1748916 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].C1CC=CC=1.[C:11]1([CH3:17])[CH:16]=CC=[CH:13][CH:12]=1>COC1C=CC(O)=CC=1>[CH:3]12[CH2:17][CH:11]([CH:12]=[CH:13]1)[CH2:16][CH:2]2[C:1]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6581Acrylic AcidHCID 7612Cyclopentadiene

Product 1

HCID 789495-Norbornene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 90154-MethoxyphenolCatalyst

Procedure

To a four-necked flask having a capacity of 1 L and equipped with a stirrer, a thermometer, and a dropping funnel, 0.40 g of p-methoxyphenol, 108.1 g (1.50 mol) of acrylic acid, and 300 mL of toluene were added, and 109.1 g (1.65 mol) of cyclopentadiene was added dropwise to the flask from the dropping funnel at 40° C. or lower over 2 hours. After completion of the addition, the resultant mixture was stirred at room temperature for 10 hours, and then concentrated under reduced pressure, to thereby obtain 167.3 g (1.21 mol) of 5-norbornene-2-carboxylic acid.

Workup

  1. customTo a four-necked flask having
  2. customa capacity of 1 L and equipped with a stirrer
  3. additionAfter completion of the addition
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-68f159e1d15d451fbb40d8b4f00d59d5
Source dataset
uspto-grants-2015_10
Patent number
US09152042B2

Reaction notes

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