Ethanol → HCID 21319305, compound

HRID 262588Notes

Reaction equation

HRID 262588 reaction equation
[Na].O[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][CH2:23][CH2:24][C:25](=[O:38])[CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1.ClCCl.C([OH:44])C>>[CH2:10]([O:9][C:7]([C:6]1[CH:12]=[CH:13][CH:3]=[CH:4][C:5]=1[O:44][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](=[O:38])[CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)=[O:8])[CH3:11]

Participants

6

Reactant 5

HCID 702Ethanol3×HCID 6344DichloromethaneHCID 8434EthylparabenHCID 5360545SodiumHCID 21319302HCID 21319302, compound

Product 1

HCID 21319305HCID 21319305, compoundYield 33%

Procedure

Sodium (0.69 g; 0.03 M.) was dissolved in absolute ethanol (30 ml.) with protection from atmospheric moisture. Ethyl 4-hydroxybenzoate (4.98 g; 0.03 M.) in absolute ethanol (20 ml.) was added and the mixture was stirred at room temperature for 30 minutes. A solution of 1-bromo-15-(4-chlorophenoxy)-pentadecan-11-one (8.62 g. 0.02 M.) in absolute ethanol (30 ml.) was added and the mixture was boiled under reflux with stirring for 8 hours. After cooling to room temperature dichloromethane (200 ml.) was added, the mixture was extracted with 5% sodium hydroxide solution (2×100 ml.) and water (1×100 ml.). The solution was dried (MgSO4), the solvent evaporated under reduced pressure and the crude product (8.75 g.) was purified by chromatography on silica-gel (300 g.) in dichloromethane to give 1-(ethoxycarbonylphenoxy)-15-(4-chlorophenoxy)-pentadecan-11-one (5.07 g.; 33%), M.P. 95°-96° C.

Workup

  1. temperatureunder reflux
  2. stirringwith stirring for 8 hours
  3. additionwas added
  4. extractionthe mixture was extracted with 5% sodium hydroxide solution (2×100 ml.) and water (1×100 ml.)
  5. dry with materialThe solution was dried (MgSO4)
  6. customthe solvent evaporated under reduced pressure
  7. customthe crude product (8.75 g.) was purified by chromatography on silica-gel (300 g.) in dichloromethane

Sources & evidence

ORD record
ord-c556c00fe885497ead5ce1da368a3f13
Source dataset
uspto-grants-1979_05
Patent number
US04154850

Reaction notes

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