Carbon Dioxide → HCID 20195523, compound

HRID 653107Notes

Reaction equation

HRID 653107 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]>O1CCCC1>[CH3:17][C:14]1[CH:15]=[CH:16][C:11]2[O:10][CH:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:19]([OH:21])=[O:20])=[CH:3][CH:4]=3)[C:12]=2[CH:13]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 5462224MagnesiumHCID 10827117HCID 10827117, compound2×

Product 1

HCID 20195523HCID 20195523, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

The product of Step B is reacted in a Grignard reaction with 5 g. of magnesium turnings in 25 ml. of tetrahydrofuran (by adding the product of Step B in 150 ml. of tetrahydrofuran at a rate sufficient to sustain refluxing). Refluxing is continued for an additional 3 hours, after which the mixture is stirred overnight at about 20° C. To this reaction mixture is added gaseous carbon dioxide over a period of 1 hour, the mixture being maintained at reflux during the second half of the hour. The reaction mixture is cooled and cautiously added to 50 ml. of 6N hydrochloric acid, then evaporated to provide a residue which is recrystallized from acetic acid to provide tan crystals of 4-(5-methyl-3-benzofuranyl)benzoic acid.

Workup

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

Sources & evidence

ORD record
ord-6185f01800314585a96993c8d881e457
Source dataset
uspto-grants-1987_06
Patent number
US04675320

Reaction notes

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