Water → Ethyl 2-ethoxy-3-(4-nitrophenyl)prop-2-enoate

HRID 1692178Notes

Reaction equation

HRID 1692178 reaction equation
[OH:1][C:2](=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)[C:3]([OH:5])=O.[C:16]([O-])([O-])=O.[Cs+].[Cs+].S(OCC)(O[CH2:26][CH3:27])(=O)=O.O.CN([CH:35]=[O:36])C>C(OCC)(=O)C>[CH2:26]([O:1][C:2](=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)[C:3]([O:36][CH2:35][CH3:16])=[O:5])[CH3:27]

Participants

7

Reactant 5

HCID 962WaterHCID 6163Diethyl SulfateHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 669053402-Hydroxy-3-(4-nitrophenyl)prop-2-enoic acid

Product 1

HCID 66905768Ethyl 2-ethoxy-3-(4-nitrophenyl)prop-2-enoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Hydroxy-3-(4-nitrophenyl)acrylic acid (20 g, 95.6 mmol) was suspended in DMF (200 ml). Cs2CO3 (74.9 g, 229.9 mmol) and diethyl sulphate (26.3 ml, 201 mmol) were added and dissolution was observed. After stirring for 18 hr at 18° C. water (350 ml) and ethyl acetate (250 ml) were added and the layers separated. The aqueous layer was further extracted with ethyl acetate (5×200 ml) then the combined organics were washed with water (2×200 ml), brine (2×200 ml) and dried over magnesium sulfate. The organics were concentrated to dryness to obtain ethyl 2-ethoxy-3-(4-nitrophenyl)-acrylate as an orange solid containing 3.6% by mass DMF (27.6 g wet, >100% yield).

Workup

  1. dissolutiondissolution
  2. additionwere added
  3. customthe layers separated
  4. extractionThe aqueous layer was further extracted with ethyl acetate (5×200 ml)
  5. washthe combined organics were washed with water (2×200 ml), brine (2×200 ml)
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe organics were concentrated to dryness

Sources & evidence

ORD record
ord-57c6e3c470774fd2b087f3f054372052
Source dataset
uspto-grants-2012_04
Patent number
US08153841B2

Reaction notes

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