Carbon Dioxide → HCID 11030140, compound

HRID 743919Notes

Reaction equation

HRID 743919 reaction equation
[Mg].[CH:2]([CH:4](Cl)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=C.[C:12](=[O:14])=[O:13].Cl.[CH2:16](OCC)C>>[CH:4]([C:5]1[CH:6]=[CH:7][C:8]([CH2:16][C:12]([OH:14])=[O:13])=[CH:9][CH:10]=1)=[CH2:2]

Participants

6

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 5462224MagnesiumHCID 11768772Benzene, 1-(chloromethyl)-3(or 4)-ethenyl-

Product 1

HCID 11030140HCID 11030140, compoundYield 22%

Conditions

Temperature
5 °C

Procedure

5.3 g (220 mmol) of magnesium turnings are mixed with 150 ml of diethyl ether under an inert nitrogen atmosphere in a 250 ml three-neck round-bottom flask. 30.5 g (200 mmol) of vinylbenzyl chloride are then added, and the mixture is refluxed for 1 hour. CO2 is then passed into the suspension, cooled to 5° C., until no exothermicity can be detected with the aid of a thermometer (about 9 g). The mixture is then poured into 400 ml of 1N hydrochloric acid and extracted twice with ether. The combined ether phases are then washed with 500 ml of water, dried over magnesium sulfate and evaporated. The resultant oil is recrystallized from a mixture of 50 ml of toluene and 150 ml of n-hexane, giving 7.1 g (22% of theory) of 4-vinylphenylacetic acid as a white powder of melting point 94° C.

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. extractionextracted twice with ether
  3. washThe combined ether phases are then washed with 500 ml of water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe resultant oil is recrystallized from a mixture of 50 ml of toluene and 150 ml of n-hexane

Sources & evidence

ORD record
ord-680c5057f9a8445ab91bc2e05f8aee07
Source dataset
uspto-grants-1996_09
Patent number
US05558978

Reaction notes

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