Ethylparaben → HCID 21319307, compound

HRID 262589Notes

Reaction equation

HRID 262589 reaction equation
[Na].[OH:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][CH:4]=1.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]#[C:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1>C(O)C>[CH2:10]([O:9][C:7]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]#[C:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]2[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=2)=[CH:13][CH:12]=1)=[O:8])[CH3:11]

Participants

5

Reactant 3

HCID 8434EthylparabenHCID 5360545SodiumHCID 21319311HCID 21319311, compound

Product 1

HCID 21319307HCID 21319307, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To a solution of sodium (0.58 g.; 0.025 M.) in absolute ethanol (15 ml.) was added ethyl 4-hydroxybenzoate (4.15 g; 0.025 M.) in absolute ethanol (20 ml.) and the mixture was stirred at room temperature for 15 minutes. A solution of 1-bromo-14-(4-chlorophenoxy)-tetradec-9-yne (7.00 g.; 0.0175 M.) in absolute ethanol (20 ml). was added and the mixture was boiled under reflux with stirring for 6 hours. The reaction mixture was cooled to room temperature filtered and the solvent removed under reduced pressure. Dichloromethane (100 ml.) was added to the residual oil, the solution was washed with 5% sodium hydroxide solution (2×100 ml.), saturated sodium chloride solution (1×100 ml.), dried and evaporated. The oil thus produced was purified by chromatography on silica-gel (250 g.) in dichloromethane to give 1-(4-ethoxycarbonylphenoxy)-14-(4-chlorophenoxy)-tetradec-9-yne (3.76 g.; 44%) M.P. 52°-53° C.

Workup

  1. additionwas added
  2. temperatureunder reflux
  3. stirringwith stirring for 6 hours
  4. temperatureThe reaction mixture was cooled to room temperature
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. additionDichloromethane (100 ml.) was added to the residual oil
  8. washthe solution was washed with 5% sodium hydroxide solution (2×100 ml.), saturated sodium chloride solution (1×100 ml.)
  9. customdried
  10. customevaporated
  11. customThe oil thus produced
  12. customwas purified by chromatography on silica-gel (250 g.) in dichloromethane

Sources & evidence

ORD record
ord-34fbc62ea9824ae2b810bf8c45158b1d
Source dataset
uspto-grants-1979_05
Patent number
US04154850

Reaction notes

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