3-(3,5-Dichlorophenyl)propionic acid → 3,5-Dichlorobenzenepropanol

HRID 480301Notes

Reaction equation

HRID 480301 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>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

4

Reactant 2

HCID 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 room temperature and 2 N NaOH (1 mL) and aqueous NH4Cl (satd., 3 mL) as 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) δ 7.17 (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. filtration2 N NaOH (1 mL) and aqueous NH4Cl (satd., 3 mL) as room temperature and 2 N NaOH (1 mL) and aqueous NH4Cl (satd., 3 mL) as over MgSO4, filtered
  4. concentrationconcentrated
  5. customThe product was purified by flash chromatography (25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-543a9ff3e18a4667919b0d5517b39617
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Reaction notes

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