Isobutylene oxide → Methyl 5-(2-hydroxy-2-methylpropoxy)-2-nitrobenzoate

HRID 2368391Notes

Reaction equation

HRID 2368391 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH3:15][C:16]1([CH3:19])[CH2:18][O:17]1.C(=O)([O-])[O-].[K+].[K+].O.P([O-])(O)(O)=O.[Na+]>C(#N)C.O>[OH:17][C:16]([CH3:19])([CH3:18])[CH2:15][O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

7

Reactant 4

HCID 11208Isobutylene oxideHCID 11430Potassium CarbonateHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 12922678Methyl 5-hydroxy-2-nitrobenzoate

Product 1

HCID 70099919Methyl 5-(2-hydroxy-2-methylpropoxy)-2-nitrobenzoateYield 29.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 5-hydroxy-2-nitrobenzoate (0.5 g, 2.54 mmol), 2,2-dimethyloxirane (6.86 ml, 7.61 mmol), potassium carbonate (351 mg, 2.54 mmol) and sodium dihydrogen phosphate monohydrate (350 mg, 2.54 mmol) in acetonitrile (4 ml) and water (0.6 ml) was stirred at 140° (5 bar) in a steel bomb for 6 hr. After cooling to r.t, the mixture was diluted with water, extracted with AcOEt, dried over MgSO4, filtered and evaporated. The crude product was purified by silica gel chromatography using a methylenechloride/MeOH gradient to obtain the title compound (200 mg, 29%) as light yellow viscous oil.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with AcOEt
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-930c728e5808487ca6c6afbe17153c53
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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