Benzene → 5-Norbornene-2-carboxylic acid

HRID 651361Notes

Reaction equation

HRID 651361 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[CH:6]1[CH2:10][CH:9]=[CH:8]C=1.[CH:11]1C=CC=CC=1>>[CH:3]12[CH2:11][CH:10]([CH:9]=[CH:8]1)[CH2:6][CH:2]2[C:1]([OH:5])=[O:4]

Participants

4

Reactant 3

HCID 241BenzeneHCID 6581Acrylic AcidHCID 7612Cyclopentadiene

Product 1

HCID 789495-Norbornene-2-carboxylic acidYield 97.9%

Procedure

In 300 ml of benzene was dissolved 324.3 g of acrylic acid. Below 40° C., 327.2 g of cyclopentadiene was added dropwise to the solution over 2 hours. After agitation was continued for 12 hours at room temperature, the reaction mixture was concentrated in vacuum, yielding 608.5 g of 5-norbornene-2-carboxylic acid. The yield was 97.9%.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuum

Sources & evidence

ORD record
ord-2ba3ca4c49954fa194012e7f2794ec91
Source dataset
uspto-grants-2001_08
Patent number
US06280898B1

Reaction notes

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