Ammonium Chloride → 3-(2,6-Dichlorophenyl)propan-1-ol

HRID 982818Notes

Reaction equation

HRID 982818 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:9]=1[CH:10]=[CH:11][C:12](OCC)=[O:13].[Cl-].[NH4+]>C1COCC1>[Cl:7][C:8]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:9]=1[CH2:10][CH2:11][CH2:12][OH:13]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4102414ethyl 2,6-dichlorocinnamateHCID 21226445Aluminium lithium hydride

Product 1

HCID 219565353-(2,6-Dichlorophenyl)propan-1-olYield 46.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (98.8 mg, 2.60 mmol) was added to THF (5 mL), and under ice-cold stirring, a solution of ethyl 2,6-dichlorocinnamate (319 mg, 1.30 mmol) in THF (5 mL) was added dropwise. The mixture was then stirred at room temperature for 30 minutes. A small amount of a saturated aqueous solution of ammonium chloride was added to the reaction mixture, followed by drying over anhydrous magnesium sulfate. Subsequent to filtration through Celite, the mixture was concentrated under reduced pressure and further, purified by chromatography on a silica gel column (hexane/ethyl acetate=10/1) to yield the title compound as a pale yellow syrupy substance (yield: 46.9%).

Workup

  1. dry with materialby drying over anhydrous magnesium sulfate
  2. filtrationSubsequent to filtration through Celite
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customfurther, purified by chromatography on a silica gel column (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-10c86e332a6f469ca1cb010daa3d96a4
Source dataset
uspto-grants-2005_03
Patent number
US06861428B2

Reaction notes

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