4-Chlorophenol → HCID 13022458, compound

HRID 426442Notes

Reaction equation

HRID 426442 reaction equation
[Na].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.Br[CH2:11][C:12]1[CH:25]=[CH:24][C:15]([O:16][CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14][CH:13]=1>C(O)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:11][C:12]2[CH:25]=[CH:24][C:15]([O:16][CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 5360545SodiumHCID 12870371Ethyl 2-[4-(bromomethyl)phenoxy]propanoate

Product 1

HCID 13022458HCID 13022458, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2.3 gm (0.1 mol) of sodium in 100 ml of ethanol was admixed at room temperature with 12.8 gm (0.1 mol) of 4-chloro-phenol, and the resulting solution was heated to its boiling point for a short time and then allowed to cool to room temperature. A solution of 28.7 gm (0.1 mol) of ethyl 2-(4-bromomethyl-phenoxy)-propionate in 20 ml of ethanol was now added while thoroughly stirring, and the mixture was boiled for a few hours, then cooled to room temperature and suction-filtered through diatomaceous earth. The filtrate was evaporated, the viscous residue was suspended in 100 ml of isopropyl ether, the suspension was suction-filtered through diatomaceous earth, and the filtrate was evaporated. The oily residue was fractionally distilled in an oil pump vacuum, yielding 71% of theory of ethyl 2-[4-(4-chlorophenoxy-methyl)-phenoxy]-propionate, b.p. 185°-190° C. at 0.1 mm Hg.

Workup

  1. temperaturethe resulting solution was heated to its boiling point for a short time
  2. waitthe mixture was boiled for a few hours
  3. temperaturecooled to room temperature
  4. filtrationsuction-filtered through diatomaceous earth
  5. customThe filtrate was evaporated
  6. filtrationthe suspension was suction-filtered through diatomaceous earth
  7. customthe filtrate was evaporated
  8. distillationThe oily residue was fractionally distilled in an oil pump vacuum

Sources & evidence

ORD record
ord-904dc3a6d2854cafb35f4ab426731734
Source dataset
uspto-grants-1979_10
Patent number
US04169720

Reaction notes

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