Sodium Iodide → Ethyl 4-docosyloxybenzoate

HRID 1196443Notes

Reaction equation

HRID 1196443 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[OH:32][C:33]1[CH:43]=[CH:42][C:36]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:35][CH:34]=1>CC(C)=O>[CH2:1]([O:32][C:33]1[CH:34]=[CH:35][C:36]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:42][CH:43]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 813551-Bromodocosane

Product 1

HCID 19898385Ethyl 4-docosyloxybenzoateYield 93.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of docosyl bromide (25 g, 0.064 mol), potassium carbonate (9.0 g) and sodium iodide (9.6 g) in acetone (150 ml), ethyl p-hydroxybenzoate (10.2 g, 0.061 mol) was added, and then reacted for 12 h under reflux with stirring. After cooling, the reaction mixture was filtered to remove inorganic materials, taken up in H2O (500 ml), and extracted with CH2Cl2 (3×100 ml). The organic layer was separated, washed with H2O, dried over MgSO4, and evaporated to dryness. The resultant residue was recrystallized from ethyl acetate to give ethyl 4-docosyloxybenzoate (27 g) as a white crystals; mp 56.5°-59.5° C. Then ethyl 4-docosyloxybenzoate (27 g) was stirred in H2O (120 ml) and ethanol (150 ml) containing sodium hydroxide (4.6 g) for 6 h under reflux. After cooling, the reaction mixture was acidified with hydrochloric acid, the resultant precipitate was filteted, washed with H2O and recrystallized from acetic acid to give the title compound as a white needles; yield: 18.5 g (72.7%); mp 99.0°-101.5° C.

Workup

  1. customreacted for 12 h
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. customto remove inorganic materials
  6. extractionextracted with CH2Cl2 (3×100 ml)
  7. customThe organic layer was separated
  8. washwashed with H2O
  9. dry with materialdried over MgSO4
  10. customevaporated to dryness
  11. customThe resultant residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-dfb579bcc65f412394fbf7d092136d47
Source dataset
uspto-grants-1992_05
Patent number
US05114615

Reaction notes

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