Carbon Dioxide → HCID 9839090, compound

HRID 1647946Notes

Reaction equation

HRID 1647946 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19](Br)[CH3:20])[CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]21[O:18]CCO2.[Mg].[C:23](=[O:25])=[O:24].Cl>O1CCCC1.O.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]([CH3:20])[C:23]([OH:25])=[O:24])[CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=[O:18]

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 5462224MagnesiumHCID 86748799HCID 86748799, compound

Product 1

HCID 9839090HCID 9839090, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

5.6 g of 1-[3-chloro-4-(2,2-ethylenedioxycyclohexane-1-yl methyl)phenyl]ethyl bromide were dissolved in 50 ml of tetrahydrofuran and added dropwise over one hour to 0.55 g of magnesium suspended in 10 ml of tetrahydrofuran, after which the whole was refluxed under agitation for three hours and cooled to produce a Grignard's reagent. The Grignard's reagent so produced was poured onto an excessive amount of solid carbon dioxide and allowed to stand still for 4 hours, after which the whole was acidified with diluted hydrochloric acid and extracted with 100 ml of ether. The extract obtained was concentrated to obtain a residue which was then incorporated with 25 ml of acetic acid and 10 ml of water and refluxed under agitation for two hours. After the end of the reaction, the reaction mixture was incorporated with 100 ml of water and extracted with 50 ml of ether. The extract obtained was washed with water, dried and freed of the solvent to obtain a residue which was then recrystallized from isopropyl ether thereby to obtain 2.7 g (yield 61%) of 2-[3-chloro-4-(2-oxocyclohexane-1-yl methyl)phenyl] propionic acid.

Workup

  1. temperatureafter which the whole was refluxed under agitation for three hours
  2. temperaturecooled
  3. customto produce a Grignard's reagent
  4. customThe Grignard's reagent so produced
  5. extractionextracted with 100 ml of ether
  6. customThe extract obtained
  7. concentrationwas concentrated
  8. customto obtain a residue which
  9. temperaturerefluxed under agitation for two hours
  10. customAfter the end of the reaction
  11. extractionextracted with 50 ml of ether
  12. customThe extract obtained
  13. washwas washed with water
  14. customdried
  15. customto obtain a residue which
  16. customwas then recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-859c76ca6de1403794e950da892d5eac
Source dataset
uspto-grants-1995_07
Patent number
US05434292

Reaction notes

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