Water → 2-Methyl-1-(4-nitrophenyl)propane-1,2-diol

HRID 522669Notes

Reaction equation

HRID 522669 reaction equation
C[N+]1([O-])CC[O:5]CC1.C([C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=1[CH:22]=[C:23]([CH3:25])[CH3:24])(C)(C)C.[OH2:26]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[CH3:24][C:23]([OH:5])([CH3:25])[CH:22]([C:14]1[CH:15]=[CH:16][C:17]([N+:19]([O-:21])=[O:20])=[CH:18][CH:13]=1)[OH:26]

Participants

6

Reactant 3

HCID 962Water2×HCID 82029Methyl morpholine oxideHCID 118023122Tert-butyl 1-(2-methylprop-1-enyl)-4-nitrobenzene

Product 1

HCID 916193172-Methyl-1-(4-nitrophenyl)propane-1,2-diolYield 100%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a solution of N-methyl morpholine-N-oxide (1.5 g, 12.8 mmol) in 4.5 mL of water was added a solution of tert-butyl 1-(2-methylprop-1-enyl)-4-nitrobenzene (1.5 g, 8.5 mmol) in acetone/water (5:1, 36 mL), followed by the addition of a solution of osmium tetraoxide in water (2 mL, 4%). This mixture was allowed to RT and stirred for 16 h. The reaction was quenched by sat. Na2SO3. aq (100 mL) and extracted with EtOAc (50 mL x 3). The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated under vacuo. The crude product (1.7 g, yield 100%) was obtained as a yellow foam, which was directly used into the next step without further purification. 1H-NMR (400 MHz, CDCl3) δ ppm 8.20 (d, 2H, J=9.2 Hz), 7.57 (d, 2H, J=9.2 Hz), 4.63 (d, 1H, J=2.4 Hz), 2.69 (d, 1H, J=3.2 Hz), 2.03 (d, 1H, J=3.2 Hz), 1.19 (s, 3H), 1.08 (s, 3H).

Workup

  1. customwas allowed to RT
  2. customThe reaction was quenched by sat. Na2SO3
  3. extractionaq (100 mL) and extracted with EtOAc (50 mL x 3)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-a682416c486b412f83a3254ca745011b
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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