Ethyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate → HCID 12804883, compound

HRID 2419159Notes

Reaction equation

HRID 2419159 reaction equation
C([O:3][C:4](=O)[CH:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[CH:10][CH:9]=1)[CH3:6])C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[Cl:22][C:16]1[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=1[O:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH:5]([CH3:6])[CH2:4][OH:3])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 12952858Ethyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 12804883HCID 12804883, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

48 g of ethyl-α-[4-(2,4-dichlorophenoxy)phenoxy]propionate was dissolved in 80 ml of anhydrous diethyl ether and the solution was added dropwise to a dispersion of 5 g of lithium aluminum hydride in 200 ml of anhydrous diethyl ether while cooling. After completion of the addition, the mixture was allowed to stand for 12 hours at room temperature and then heated under refluxing for 1.5 hours to complete the reaction. The reaction mixture was poured into an appropriate amount of ice water, and the ethereal layer was separated. The ethereal layer was again extracted with diethyl ether and the extract was dried over anhydrous sodium sulfate. The ether was removed by distillation from the dried extract, and the residue was distilled under reduced pressure to obtain 40 g of the desired product having a boiling point of 201° to 205° C/2 mmHg.

Workup

  1. temperaturewhile cooling
  2. additionAfter completion of the addition
  3. temperatureheated
  4. temperatureunder refluxing for 1.5 hours
  5. customthe reaction
  6. customthe ethereal layer was separated
  7. extractionThe ethereal layer was again extracted with diethyl ether
  8. dry with materialthe extract was dried over anhydrous sodium sulfate
  9. customThe ether was removed by distillation from the dried
  10. extractionextract
  11. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-949aab61a234455f85084eeddf16482e
Source dataset
uspto-grants-1978_08
Patent number
US04105435

Reaction notes

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