Acetone → Benzoic acid, m-(2,3-dihydroxypropoxy)-, methyl ester

HRID 2180242Notes

Reaction equation

HRID 2180242 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])C=C.C[N+]1([O-])CC[O:19]CC1.[CH3:23][C:24]([CH3:26])=[O:25]>[Os](=O)(=O)(=O)=O.O>[OH:25][CH:24]([CH2:26][OH:19])[CH2:23][O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 3

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 10932265Methyl 3-(allyloxy)benzoate

Product 1

HCID 49017Benzoic acid, m-(2,3-dihydroxypropoxy)-, methyl ester

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

A solution of Example 460A (0.3 g, 1.5 mmol), 4-methylmorpholine N-oxide (0.55 g, 4.5 mmol) and osmium tetroxide (4 wt % solution in water 0.1 mL, 0.015 mmol) in 9:1/acetone:water was stirred at room temperature for 48 h. The reaction was quenched with 10% Na2S2O3 and stirred for 15 minutes, extracted with ethyl acetate, washed with brine, dried (Na2SO4), and concentrated to give the title compound.

Workup

  1. customThe reaction was quenched with 10% Na2S2O3
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-99873ade8f1f4dc294174d66c1c698de
Source dataset
uspto-grants-2005_05
Patent number
US06887863B2

Reaction notes

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