Methanol → 4-(2,3-Dihydroxypropyl)-3-methoxybenzonitrile

HRID 1519594Notes

Reaction equation

HRID 1519594 reaction equation
[CH2:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[O:12][CH3:13])C=C.C[N+]1([O-])CC[O:18][CH2:17]C1.[CH3:22][OH:23]>O.O=[Os](=O)(=O)=O>[OH:23][CH:22]([CH2:17][OH:18])[CH2:1][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[O:12][CH3:13]

Participants

6

Reactant 3

HCID 887MethanolHCID 82029Methyl morpholine oxideHCID 675133484-Allyl-3-methoxybenzonitrile

Product 1

HCID 675137884-(2,3-Dihydroxypropyl)-3-methoxybenzonitrile

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

To a solution of 4-allyl-3-methoxybenzonitrile (1.1 g, 6.4 mmol) in 30 mL of methanol and 10 mL of water was added OsO4 (140 mg) and NMO (2.2 g, 16 mmol), and the mixture was stirred at ambient temperature overnight. Remove the methanol under reduced pressure, the residue was dissolved in EtOAc, washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by fast column chromatograph to give 4-(2,3-dihydroxypropyl)-3-methoxybenzonitrile. MS m/z: 208 (M+1)+.

Workup

  1. customRemove the methanol under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by fast column chromatograph

Sources & evidence

ORD record
ord-edd16adcc06449d692b2aab77a693426
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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