Ethyl Acetate → HCID 70873815, compound

HRID 2208920Notes

Reaction equation

HRID 2208920 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([N+:13]([O-:15])=[O:14])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:23][CH2:24][OH:25].C(OCC)(=O)C>C(#N)C.O>[OH:25][CH2:24][CH2:23][O:1][C:2]1[CH:3]=[C:4]([N+:13]([O-:15])=[O:14])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 108982-BromoethanolHCID 23009748Methyl 5-hydroxy-2-methyl-3-nitrobenzoate

Product 1

HCID 70873815HCID 70873815, compoundYield 74.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 5-hydroxy-2-methyl-3-nitrobenzoate (1.5 g, 7.1 mmol) in ACN (15 mL), were added cesium carbonate (4.6 g, 14 mmol) and 2-bromoethanol (2.5 mL, 35 mmol). The resulting reaction mixture was heated at 80° C. overnight. On completion, the reaction mixture was diluted with water and extraction was carried out using ethyl acetate. The combined organic layers were washed with water, dried and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography to afford the title compound (1.35 g, 74%).

Workup

  1. customThe resulting reaction mixture
  2. washThe combined organic layers were washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dbb75da19b1643d8af6cccf02d70ae64
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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