Carbon Dioxide → Benzoic acid, 3-ethyl-

HRID 1727341Notes

Reaction equation

HRID 1727341 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 minutes under the same condition. The reaction mixture was added to crashed dry ice, and the mixture was stirred for 1 hour. To the reaction mixture was added 1N-hydrochloric acid, and extracted with ethyl acetate. The extracts were dried, filtrated and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=5:1) to obtain a title compound (3.87 g, yield 93%).

Workup

  1. additionThe reaction mixture was added
  2. stirringthe mixture was stirred for 1 hour
  3. extractionextracted with ethyl acetate
  4. customThe extracts were 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-2acd0e5b52b948f1b0aeaaf1a619904d
Source dataset
uspto-grants-2009_02
Patent number
US07495018B2

Reaction notes

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