Benzyl 4-Hydroxybenzoate → HCID 18381591, compound

HRID 2297386Notes

Reaction equation

HRID 2297386 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:25][C:26]([O:28][CH2:29]C)=[O:27]>CC(C)=O>[CH3:29][O:28][C:26]([CH2:25][O:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1)=[O:27]

Participants

5

Reactant 3

HCID 7180Benzyl 4-HydroxybenzoateHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonate

Product 1

HCID 18381591HCID 18381591, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4.5 g (0.02 mol) of benzyl p-hydroxybenzoate were suspended in about 60 ml of acetone together with 9.7 g (0.03 mol) of cesium carbonate and treated with 2.3 ml (0.025 mol) of ethyl bromoacetate. The mixture was then refluxed until reaction was complete. For working-up, the reaction solution was filtered through a clarifying layer and the filtrate was concentrated to dryness. The residue was taken up in ethyl acetate and the mixture was washed three times each with 10% strength citric acid solution and saturated NaCl solution. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was recrystallized from diisopropyl ether/heptane. Yield: 5.5 g.

Workup

  1. temperatureThe mixture was then refluxed until reaction
  2. filtrationthe reaction solution was filtered through a clarifying layer
  3. concentrationthe filtrate was concentrated to dryness
  4. washthe mixture was washed three times each with 10% strength citric acid solution and saturated NaCl solution
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was recrystallized from diisopropyl ether/heptane

Sources & evidence

ORD record
ord-dfdb427bb8ce440ebb975198cd5be19a
Source dataset
uspto-grants-2002_12
Patent number
US06492356B1

Reaction notes

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