3-(2-Oxopropyl)benzoic acid → 3-(2-Hydroxy-2-methylpropyl)benzoic acid

HRID 385255Notes

Reaction equation

HRID 385255 reaction equation
C[Mg+].[Br-].[O:4]=[C:5]([CH3:16])[CH2:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11].[CH2:17](Cl)Cl.CO>C1COCC1.O>[OH:4][C:5]([CH3:17])([CH3:16])[CH2:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11]

Participants

6

Reactant 3

HCID 122541053-(2-Oxopropyl)benzoic acidHCID 21226129Dichloromethane methanolHCID 178418689HCID 178418689, compound

Product 1

HCID 575175823-(2-Hydroxy-2-methylpropyl)benzoic acidYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

CH3MgBr (3.0 M in THF, 11.2 mL, 33.7 mmol) was added slowly to a stirring solution of 3-(2-oxopropyl)benzoic acid (2 g, 11.2 mmol) in THF (100 mL) at 0° C. The resulting suspension was allowed to warm to rt then stirred overnight. The reaction mixture was diluted with H2O (50 mL) then quenched with 5 N HCl (pH<3). The aqueous layer was extracted with EtOAc (3×50 mL). The combined organic layers were washed with H2O (100 mL), brine (100 mL), dried over Na2SO4 (s), and concentrated to give a yellow oil. Chromatography (9:1, CH2Cl2/MeOH) afforded the title compound (1.36 g, 62%) as a white solid. ES/MS calcd. for C11H14NaO3+ 217.1. found m/z=217.2 (M+Na)+.

Workup

  1. customthen quenched with 5 N HCl (pH<3)
  2. extractionThe aqueous layer was extracted with EtOAc (3×50 mL)
  3. washThe combined organic layers were washed with H2O (100 mL), brine (100 mL)
  4. dry with materialdried over Na2SO4 (s)
  5. concentrationconcentrated
  6. customto give a yellow oil

Sources & evidence

ORD record
ord-45d8464205384ce48b090be4acbc5a61
Source dataset
uspto-grants-2013_02
Patent number
US08367829B2

Reaction notes

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