2-Methyl-4-nitrophenol → HCID 45097887, compound

HRID 1393105Notes

Reaction equation

HRID 1393105 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[CH3:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:9]=1[OH:17].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[CH3:6][O:5][C:3](=[O:4])[CH2:2][O:17][C:9]1[CH:10]=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:8]=1[CH3:7]

Participants

5

Reactant 3

HCID 74422-Methyl-4-nitrophenolHCID 10796Cesium carbonateHCID 60984Methyl bromoacetate

Product 1

HCID 45097887HCID 45097887, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of methyl bromoacetate (15.76 ml, 171 mmol) and 2-methyl-4-nitrophenol (25.0 g, 163 mmol) in dry acetonitrile (300 ml) was treated with Cs2CO3 (61.3 g, 188 mmol) and stirred at RT for 4 h. The mixture was filtered, washed with acetonitrile and evaporated. The residue was suspended in CH2Cl2 (700 ml), filtered and evaporated to give 36.4 g of (2-methyl-4-nitro-phenoxy)-acetic acid methyl ester as yellow crystals, MS: 225 M+.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with acetonitrile
  3. customevaporated
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-f4c96ebf306e42749d8c756be813deed
Source dataset
uspto-grants-2008_03
Patent number
US07345067B2

Reaction notes

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