(2,4-Dichlorophenoxy)Acetic Acid → 2-(2,4-Dichlorophenoxy)ethanol

HRID 1985280Notes

Reaction equation

HRID 1985280 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6](O)=[O:7]>O1CCCC1>[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][CH2:6][OH:7]

Participants

3

Reactant 1

HCID 1486(2,4-Dichlorophenoxy)Acetic Acid

Product 1

HCID 84442-(2,4-Dichlorophenoxy)ethanolYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 15.0 g of 2,4-dichlorophenoxyacetic acid in tetrahydrofuran (300 ml) was added dropwise 96 ml of 1.0 M borane-tetrahydrofuran complex/tetrahydrofuran solution under ice-cooling over 1.5 hours. The reaction solution was stirred at room temperature for 22 hours. After the reaction solution was concentrated, the residue was diluted with saturated aqueous ammonium chloride and ethyl acetate. The organic layer was washed with saturated ammonium chloride, saturated aqueous sodium hydrogen carbonate (×2) and saturated ammonium chloride, then dried over anhydrous sodium sulfate and concentrated, to give 14 g the title compound as a colorless oil.

Workup

  1. temperaturecooling over 1.5 hours
  2. concentrationAfter the reaction solution was concentrated
  3. additionthe residue was diluted with saturated aqueous ammonium chloride and ethyl acetate
  4. washThe organic layer was washed with saturated ammonium chloride, saturated aqueous sodium hydrogen carbonate (×2) and saturated ammonium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1a921dd2d71147e484c5ecf6a8b84a2d
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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