Potassium Carbonate → 1-(3-Nitrophenyl)-1,2-ethanediol

HRID 221402Notes

Reaction equation

HRID 221402 reaction equation
C([O:4][CH2:5][CH:6]([OH:16])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO>[N+:13]([C:9]1[CH:8]=[C:7]([CH:6]([OH:16])[CH2:5][OH:4])[CH:12]=[CH:11][CH:10]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 583788672-Hydroxy-2-(3-nitrophenyl)ethyl acetate

Product 1

HCID 149970311-(3-Nitrophenyl)-1,2-ethanediolYield 88.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

2-Hydroxy-2-(3-nitrophenyl)ethyl acetate (18 g) was dissolved in MeOH (180 mL) and cooled to 0° C. K2CO3 (22 g) was added and the reaction stirred at room temperature for 2 hours. The mixture was concentrated under vacuum, quenched by addition of water (100 mL) and extracted with ethyl acetate (2×100 mL). The EtOAc layer was dried over Na2SO4 and concentrated to give the crude title compound (13 g, 88%).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customquenched by addition of water (100 mL)
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. dry with materialThe EtOAc layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c5d8b55df41e48bc9b223b714c1c20f2
Source dataset
uspto-grants-2012_06
Patent number
US08207167B2

Reaction notes

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