Sodium Hydroxide → 3,5-Dichlorobenzenepropanol

HRID 1699024Notes

Reaction equation

HRID 1699024 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:9]=[C:10]([CH2:15][CH2:16][C:17](O)=[O:18])[CH:11]=[C:12]([Cl:14])[CH:13]=1.[OH-].[Na+].[NH4+].[Cl-]>CCOCC>[Cl:7][C:8]1[CH:9]=[C:10]([CH2:15][CH2:16][CH2:17][OH:18])[CH:11]=[C:12]([Cl:14])[CH:13]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 8193053-(3,5-Dichlorophenyl)propionic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 145813153,5-DichlorobenzenepropanolYield 31.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

LiAlH4 (1M in Et2O, 10 mL, 10 mmol) was slowly added to a solution of 3-(3,5-dichlorophenyl)-propionic acid (2.19 g, 10 mmol) in Et2O (50 mL). The reaction was heated at reflux for 2 h. The reaction was cooled to room temperature and 2 N NaOH (1 mL) and aqueous NH4Cl (satd., 3 mL) as carefully added. The solution was filtered through Celite and the filtrate was dried over MgSO4, filtered, and concentrated. The product was purified by flash chromatography (25% EtOAc/hexanes) to afford 3-(3,5-dichlorophenyl)-propanol (640 mg). 1H NMR (400 MHz, CDCl3) δ7.17 (m, 1H), 7.07 (m, 2H), 3.64 (m, 2H), 2.65 (t, 2H), 1.84 (m, 2H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2 h
  3. filtrationThe solution was filtered through Celite
  4. dry with materialthe filtrate was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was purified by flash chromatography (25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-25d4e8c5afe5493a8028c6297b704b82
Source dataset
uspto-grants-2002_02
Patent number
US06344485B1

Reaction notes

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