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

HRID 1348786Notes

Reaction equation

HRID 1348786 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 column chromatography on silica gel (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 column chromatography on silica gel (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-055da303cee9464899c79e9ab562d0b8
Source dataset
uspto-grants-2007_05
Patent number
US07211577B2

Reaction notes

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