Carbon Dioxide → HCID 21320303, compound

HRID 262229Notes

Reaction equation

HRID 262229 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:11]=3[O:10][CH:9]=2)=[CH:4][CH:3]=1.[Mg].[C:19](=[O:21])=[O:20].Cl>O1CCCC1>[CH3:17][C:14]1[CH:15]=[CH:16][C:11]2[O:10][CH:9]=[C:8]([C:5]3[CH:4]=[C:3]([CH:2]=[CH:7][CH:6]=3)[C:19]([OH:21])=[O:20])[C:12]=2[CH:13]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 5462224MagnesiumHCID 10827117HCID 10827117, compound

Product 1

HCID 21320303HCID 21320303, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

The product of step B in 150 ml. of tetrahydrofuran is added to 5 g. of magnesium turnings in 25 ml. of tetrahydrofuran at a rate sufficient to sustain refluxing. Refluxing is continued for an additional three hours, then the mixture is stirred overnight at about 20° C. To this reaction mixture is added gaseous carbon dioxide over a period of one hour. The mixture is maintained at reflux during the second half hour. The reaction mixture is cooled and cautiously added to 50 ml. of 6N hydrochloric acid. The reaction mixture is evaporated to provide a residue which is recrystallized from acetic acid to provide tan crystals of 3-(5-methyl-3-benzofuranyl)benzoic acid.

Workup

  1. temperatureRefluxing
  2. temperatureThe mixture is maintained
  3. temperatureat reflux during the second half hour
  4. temperatureThe reaction mixture is cooled
  5. additioncautiously added to 50 ml
  6. customThe reaction mixture is evaporated
  7. customto provide a residue which
  8. customis recrystallized from acetic acid

Sources & evidence

ORD record
ord-8d3f7953f1d74ea7a7e603e4628b2b4b
Source dataset
uspto-grants-1979_05
Patent number
US04153716

Reaction notes

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