Water → m-Chlorophenethylic alcohol

HRID 2292110Notes

Reaction equation

HRID 2292110 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]([CH2:14][C:15](O)=[O:16])[CH:11]=[CH:12][CH:13]=1.O>CCOCC>[Cl:7][C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][OH:16])[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 158793-Chlorophenylacetic acidHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 78856m-Chlorophenethylic alcoholYield 99.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Lithium aluminium hydride (19 g,) was suspended in dry ether (300 ml) and 3-chlorophenylacetic acid (58 g,) in dry ether (600 ml) was added dropwise to the stirred suspension over 1 hr. The mixture was then heated at reflux for 2 hr. when tlc indicated completion of reaction. Excess lithum aluminium hydride was carefully decomposed with water (500 ml). The ether layer was separated off and 2M hydrochloric acid was used to break up the gelatinous aqueous layer which was then extracted with ether (2×400 ml). The combined ether layers were washed with water (300 ml), dried (sodium sulphate) and evaporated in vacuo to give 2-(3-chlorophenyl)ethanol as a pale yellow oil (53.1 g) characterised by its nmr spectrum.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 2 hr
  3. customcompletion of reaction
  4. customThe ether layer was separated off
  5. extractionwas then extracted with ether (2×400 ml)
  6. washThe combined ether layers were washed with water (300 ml)
  7. dry with materialdried (sodium sulphate)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-76c831d3af1b44569612e66177534a5b
Source dataset
uspto-grants-1989_01
Patent number
US04801593

Reaction notes

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