Potassium Carbonate → Phenyl 4-(2-phenoxyethoxy)benzoate

HRID 2377259Notes

Reaction equation

HRID 2377259 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[O:17]([CH2:24][CH2:25]Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[O:17]([CH2:24][CH2:25][O:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68526Benzene, (2-bromoethoxy)-HCID 87250Phenylparaben

Product 1

HCID 23011964Phenyl 4-(2-phenoxyethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of phenyl 4-hydroxybenzoate (2.14 g, 10 mmol), 2-phenoxyethyl bromide (12.1 g, 60 mmol) and potassium carbonate (4.1 g, 30 mmol) in 1,4-dioxane (60 mL) was heated to reflux for about 2 days. The mixture was cooled, filtered and concentrated under vacuum. The residue was purified by flash chromatography on silica gel using hexane/ethyl acetate (3:1) as eluent to provide the desired product. 1H NMR (500 MHz, CDCl3) δ 4.39 (m, 2H), 4.42 (m, 2H), 6.97 (d, J=8 Hz, 2H), 6.99 (t, J=8 Hz, 1H), 7.03 (d, J=8 Hz, 2H), 7.21 (d, J=8 Hz, 2H), 7.25 (m, 1H), 7.35 (t, J=8 Hz, 2H), 7.42 (t, J=8 Hz, 2H), 8.17 (d, J=8 Hz, 2H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for about 2 days
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-231401704d2c45a485d378b090137c34
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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