Triethylamine → 2-(3,4-Dichlorophenyl)ethanol

HRID 1106859Notes

Reaction equation

HRID 1106859 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]([CH2:15][C:16](O)=[O:17])[CH:11]=[CH:12][C:13]=1[Cl:14].C(N(CC)CC)C.[OH-].[Na+]>O1CCCC1.O>[Cl:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][C:13]=1[Cl:14])[CH2:15][CH2:16][OH:17]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 798743,4-Dichlorophenylacetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 2445582-(3,4-Dichlorophenyl)ethanolYield 88.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (LAH) (0.57 g, 0.015 mol) were dissolved in tetrahydrofuran (30 ml) at room temperature, followed by stirring for 30 min. To the resulting solution there was slowly added dropwise a solution having 3,4-dichlorophenylacetic acid (3 g, 0.015 mol) and triethylamine (2.1 ml, 0.015 mol) dissolved in tetrahydrofuran (20 ml) and after stirring at the reflux temperature for 3 h, the mixture was cooled and water was poured into. The mixture was neutralized with an aqueous solution of sodium hydroxide and subjected to extraction with ethyl acetate to yield the end compound 3,4-dichlorophenethyl alcohol (2.53 g).

Workup

  1. additionTo the resulting solution there was slowly added dropwise a solution
  2. stirringafter stirring at the reflux temperature for 3 h
  3. temperaturethe mixture was cooled
  4. extractionsubjected to extraction with ethyl acetate

Sources & evidence

ORD record
ord-3fb5fd3134c14c5d8aa8b561a0c961f9
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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