Carbon Dioxide → Benzoic acid, 3-ethyl-

HRID 1268721Notes

Reaction equation

HRID 1268721 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH3:9])[CH:3]=1.[Mg].[C:11](=[O:13])=[O:12].Cl>O1CCCC1>[CH2:8]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[C:11]([OH:13])=[O:12])[CH3:9]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 123170Benzene, 1-bromo-3-ethyl-HCID 5462224Magnesium

Product 1

HCID 96207Benzoic acid, 3-ethyl-Yield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an argon atmosphere, a solution of 1-bromo-3-ethylbenzene (5.1 g, 28 mmol) in tetrahydrofuran (45 mL) was added dropwise to a mixture of magnesium turnings (0.74 g, 31 mmol) in tetrahydrofuran (5.0 mL), and the mixture was stirred for 30 min. The reaction mixture was added to crushed dry ice and stirred for 1 hr. 1N Hydrochloric acid was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was dried, filtered and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=5:1) to give the title compound (3.87 g, yield 93%).

Workup

  1. additionThe reaction mixture was added
  2. stirringstirred for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe extract was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=5:1)

Sources & evidence

ORD record
ord-2a4f0d65f633427c8713759b7679a272
Source dataset
uspto-grants-2007_04
Patent number
US07199124B2

Reaction notes

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