Ethylparaben → Ethyl 4-{[7-(4-chlorophenoxy)heptyl]oxy}benzoate

HRID 262586Notes

Reaction equation

HRID 262586 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][O:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=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][O:22][C:23]2[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=2)=[CH:13][CH:12]=1)=[O:8])[CH3:11]

Participants

5

Reactant 3

HCID 8434EthylparabenHCID 5360545SodiumHCID 129864911-Bromo-7-(4-chlorophenoxy)-heptane

Product 1

HCID 71369541Ethyl 4-{[7-(4-chlorophenoxy)heptyl]oxy}benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

Sodium (2.5 g., 0.11 M) was dissolved in absolute ethanol (50 ml) and ethyl 4-hydroxybenzoate (16.6 g., 0.10 M) in ethanol (50 ml) was added at room temperature. The mixture was stirred at room temperature for 15 min, 1-bromo-7-(4-chlorophenoxy)-heptane (0.10 M) in ethanol (50 ml) was added in one portion and the mixture was boiled under reflux with stirring for 24 hours. The hot solution was filtered to remove sodium bromide, the ethanol removed under vacuum, the product dissolved in dichloromethane (100 ml) and washed with 5% sodium hydroxide solution (2×100 ml) and water (2×100 ml). The dichloromethane solution was dried (MgSO4), filtered, evaporated and the product purified by crystallisation, from ethanol m.p. 70°-71°.

Workup

  1. temperatureunder reflux
  2. stirringwith stirring for 24 hours
  3. filtrationThe hot solution was filtered
  4. customto remove sodium bromide
  5. customthe ethanol removed under vacuum
  6. dissolutionthe product dissolved in dichloromethane (100 ml)
  7. washwashed with 5% sodium hydroxide solution (2×100 ml) and water (2×100 ml)
  8. dry with materialThe dichloromethane solution was dried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customthe product purified by crystallisation, from ethanol m.p. 70°-71°

Sources & evidence

ORD record
ord-f648f8f624b04163b68b6d935139a87e
Source dataset
uspto-grants-1979_05
Patent number
US04154850

Reaction notes

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