Methyl Ethyl Ketone → Methyl-5-norbornene-2-carboxylic acid

HRID 991019

Reaction equation

HRID 991019 reaction equation
[CH3:1][C:2]1[CH2:6][CH:5]=[CH:4][CH:3]=1.[C:7]([OH:11])(=[O:10])C=C.[CH2:12](C(C)=O)[CH3:13]>>[CH3:1][C:2]12[CH2:6][CH:5]([CH:12]=[CH:13]1)[CH2:4][CH:3]2[C:7]([OH:11])=[O:10]

Participants

4

Reactant 3

HCID 6569Methyl Ethyl KetoneHCID 6581Acrylic AcidHCID 667751-Methyl-1,3-cyclopentadiene

Product 1

HCID 18417281Methyl-5-norbornene-2-carboxylic acid

Procedure

Methylcyclopentadiene (8.01 g: 100 mmol) was dissolved in methyl ethyl ketone (10 mL), to which acrylic acid (7.93 g: 110 mmol) was added dropwise at 0° C. over 1 hour. The thus-obtained mixture was stirred at room temperature for 3 hours. Light components, such as the solvent and unreacted acrylic acid, were then distilled off under reduced pressure from the reaction mixture, whereby methyl-5-norbornene-2-carboxylic acid (14.9 g: 98 mmol) was obtained.

Workup

  1. additionwas added dropwise at 0° C. over 1 hour
  2. distillationLight components, such as the solvent and unreacted acrylic acid, were then distilled off under reduced pressure from the reaction mixture

Sources & evidence

ORD record
ord-5ca62e95097e4bfab6ef6fddcc2ae1a2
Source dataset
uspto-grants-2002_10
Patent number
US06462158B1

Linked notes

Loading…