Sodium Carbonate → Phenyl 4-[2-(2-methoxyethoxy)ethoxy]benzoate

HRID 2377258Notes

Reaction equation

HRID 2377258 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.[H-].[Na+].Br[CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[CH3:26][O:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20][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

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 87250PhenylparabenHCID 1235321-Bromo-3,6-dioxaheptane

Product 1

HCID 69202991Phenyl 4-[2-(2-methoxyethoxy)ethoxy]benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of phenyl 4-hydroxybenzoate (2.1 g, 9.8 mmol) in tetrahydrofuran (40 mL) was added a 60% suspension of sodium hydride in mineral oil (408 mg, 10.2 mmol) and the mixture was stirred at room temperature for about 30 minutes. Then 1-bromo-2-(2-methoxyethoxy)ethane (2.5 g, 13.7 mmol) was added and stirring was continued for about 5 days. The mixture was poured into saturated aqueous sodium carbonate and was extracted with ethyl acetate, the combined organic extracts were washed with saturated aqueous sodium carbonate, dried (Na2SO4), filtered, and concentrated under vacuum. The residue was purified by flash chromatography on silica gel using hexane/ethyl acetate (10:1) as eluent to provide the desired product. 1H NMR (500 MHz, CDCl3) δ 3.40 (s, 3H), 3.60 (m, 2H), 3.76 (m, 2H), 3.92 (t, J=8 Hz, 2H), 4.22 (t, J=8 Hz, 2H), 7.00 (d, J=8 Hz, 2H), 7.22 (m, 3H), 7.42 (d, J=8 Hz, 2H), 8.17 (d, J=8 Hz, 2H).

Workup

  1. stirringstirring
  2. waitwas continued for about 5 days
  3. extractionwas extracted with ethyl acetate
  4. washthe combined organic extracts were washed with saturated aqueous sodium carbonate
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-ab33dc03484642cd942b6d262880b18b
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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