Carbon Dioxide → Benzoic acid, 3-ethyl-

HRID 1062643Notes

Reaction equation

HRID 1062643 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

A solution (45 mL) of 1-bromo-3-ethylbenzene (5.1 g, 28 mmol) in tetrahydrofuran was added dropwise to a mixture (5.0 mL) of magnesium turnings (0.74 g, 31 mmol) and tetrahydrofuran under an argon atmosphere, and the mixture was stirred as it was for 30 min. The reaction mixture was added to the crushed dry ice and the mixture was stirred as it was for 1 h. 1N Hydrochloric acid was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was dried, filtrated 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%). oil.

Workup

  1. stirringthe mixture was stirred as it
  2. waitwas for 1 h
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe extract was dried
  5. filtrationfiltrated
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=5:1)

Sources & evidence

ORD record
ord-55867fb638f04e88989ba04dcdd31791
Source dataset
uspto-grants-2005_11
Patent number
US06962933B1

Reaction notes

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