4-Formylbenzoic acid → HCID 59811331, compound

HRID 2113635Notes

Reaction equation

HRID 2113635 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([OH:3])=[O:2].[CH2:12]([Mg]Cl)[C:13]([CH3:16])([CH3:15])[CH3:14]>C1COCC1.CCCCCC>[CH3:12][C:13]([CH3:16])([CH3:15])/[CH:14]=[CH:8]/[C:7]1[CH:10]=[CH:11][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 120884-Formylbenzoic acidHCID 178418809HCID 178418809, compound

Product 1

HCID 59811331HCID 59811331, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a cooled (0° C.) and well stirred suspension of 4-carboxy benzaldehyde (2.0 g, 13.32 mmol) in anhydrous THF (90 mL) is added 33.3 mmol of neopentyl magnesium chloride in hexane during 20 minutes and the mixture is stirred at the same temperature for an additional two hours before being quenched with satyrated ammonium chloride solution. Most of the THF is evaporated and the aqueous mixture is treated with conc. HCl (50 mL) and the mixture is heated to reflux for 2 hours. The mixture is then cooled to ambient temperature and extracted with methylene chloride (2×100 mL), the organic layer is dried over sodium sulfate and concentrated to obtain the desired 4-(3,3-dimethyl-but-1-enyl)-benzoic acid.

Workup

  1. temperatureTo a cooled
  2. custombefore being quenched with satyrated ammonium chloride solution
  3. customMost of the THF is evaporated
  4. additionthe aqueous mixture is treated with conc. HCl (50 mL)
  5. temperaturethe mixture is heated
  6. temperatureto reflux for 2 hours
  7. extractionextracted with methylene chloride (2×100 mL)
  8. dry with materialthe organic layer is dried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-5e3a67fe2e2b4ebd808f0de389894432
Source dataset
uspto-grants-2008_10
Patent number
US07432281B2

Reaction notes

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