2-Methyl-4-nitrophenol → 2-Methyl-1-(2-methyl-4-nitrophenoxy)propan-2-ol

HRID 562596

Reaction equation

HRID 562596 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[CH3:12][C:13]1([CH3:16])[CH2:15][O:14]1.C([O-])([O-])=O.[K+].[K+]>CC#N.O.C([O-])(O)=O.[Na+]>[CH3:12][C:13]([OH:14])([CH3:16])[CH2:15][O:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[CH3:1]

Participants

7

Reactant 3

HCID 74422-Methyl-4-nitrophenolHCID 11208Isobutylene oxideHCID 11430Potassium Carbonate

Product 1

HCID 575406062-Methyl-1-(2-methyl-4-nitrophenoxy)propan-2-olYield 90.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 2-methyl-4-nitrophenol (5.50 g, 35.9 mmol), 2,2-dimethyloxirane (7.77 g, 108 mmol), K2CO3 (4.96 g, 35.9 mmol) and NaH2PO4 (4.31 g, 35.9 mmol) in MeCN (50 mL) and H2O (8.82 mL) was stirred at 140° C. in a steel bomb for 6 hours. After cooling to RT, the reaction was diluted with aq. saturated NaHCO3 (80 ml) prior to extraction with EtOAc (100 ml). The EtOAc layer was dried over Na2SO4 and concentrated. The crude product was purified by silica gel chromatography employing a solvent gradient (hexane to 60% ethyl acetate) to elute 2-methyl-1-(2-methyl-4-nitrophenoxy)propan-2-ol (7.3 g, 32.4 mmol, 90% yield) as yellow oil. MS (M+1=226). 1H NMR (500 MHz, chloroform-d) δ ppm 8.00-8.15 (2H, m), 6.86 (1H, d, J=8.80 Hz), 3.90 (2H, s), 2.33 (3H, s), 1.40 (6H, s).

Workup

  1. extractionto extraction with EtOAc (100 ml)
  2. dry with materialThe EtOAc layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4c1de9f843dd41b79fa4927fad584c96
Source dataset
uspto-grants-2011_11
Patent number
US08067420B2

Linked notes

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