1-Bromooctane → HCID 14745587, compound

HRID 1074112Notes

Reaction equation

HRID 1074112 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[O-]CC.[Na+].[CH2:18](Br)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C(O)C>[CH2:18]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 28310Ethyl 4-hydroxyphenylacetateHCID 2723922Sodium ethoxide

Product 1

HCID 14745587HCID 14745587, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The ethyl 4-hydroxyphenylacetate (59 g) and sodium ethoxide (22.4 g) are dissolved in ethanol (150 ml) and thereto is added n-octyl bromide (63.5 g), and the mixture is refluxed for 3 hours and concentrated under reduced pressure, and thereto is added ethyl acetate to dissolve the oily substance. The mixture is washed with water, dried over anhydrous magnesium sulfate, distilled under reduced pressure to remove ethyl acetate, and further distilled under reduced pressure to give ethyl 4-n-octyloxyphenylacetate (79.6 g, b.p. 179° C./0.1 mmHg).

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. concentrationconcentrated under reduced pressure
  3. additionis added ethyl acetate
  4. dissolutionto dissolve the oily substance
  5. washThe mixture is washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationdistilled under reduced pressure
  8. customto remove ethyl acetate
  9. distillationfurther distilled under reduced pressure

Sources & evidence

ORD record
ord-a407cf90150b4e4c85c241c133eb3e71
Source dataset
uspto-grants-1990_11
Patent number
US04973425

Reaction notes

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