Heptane → 2-Isobutyryl-3-methyl-benzoic acid

HRID 1047847Notes

Reaction equation

HRID 1047847 reaction equation
Br[C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CCCCCCC.[Li]CCCC.CCCCCC.[C:30](Cl)(=[O:34])[CH:31]([CH3:33])[CH3:32]>C1COCC1>[C:30]([C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])(=[O:34])[CH:31]([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 8900HeptaneHCID 62325Isobutyryl chlorideHCID 27355882-Bromo-3-methylbenzoic acidHCID 178418244HCID 178418244, compound

Product 1

HCID 593141812-Isobutyryl-3-methyl-benzoic acidYield 58.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of 2-bromo-3-methyl-benzoic acid (1.5 g, 6.98 mmol) in 10 mL THF is treated with 1M Bu2Mg/heptane at −15° C. under argon. After stirring for 30 min, 1.6M n-BuLi/hexane is added dropwise at −15° C. and the mixture is left for 1 hr. Then isobutyryl chloride (2.95 ml, 27.9 mmol) is added dropwise. After another 30 min stirring, the reaction is quenched with 2N HCl aqueous solution (2 ml). After concentration, the residue is purified by HPLC to give a pure product (227) as white solid (840 mg, 58%).

Workup

  1. waitthe mixture is left for 1 hr
  2. stirringAfter another 30 min stirring
  3. customthe reaction is quenched with 2N HCl aqueous solution (2 ml)
  4. concentrationAfter concentration
  5. customthe residue is purified by HPLC

Sources & evidence

ORD record
ord-836175aee40d4ca8b4f4541a62143c4f
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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