Sodium Hydroxide → m-Chlorophenethylic alcohol

HRID 1620986Notes

Reaction equation

HRID 1620986 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9](O)=[O:10])[CH:5]=[CH:6][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 158793-Chlorophenylacetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 78856m-Chlorophenethylic alcoholYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-(3-chlorophenyl)acetic acid (11.4 g, 66.7 mmol) in 150 mL of THF was added LiAlH4 (3.04 g, 80.0 mmol) portionwise at 0° C. The resulting mixture was warmed to room temperature and stirred for 2 hours under N2 atmosphere. Then 2 N NaOH (30 mL) was added dropwise and extracted with EtOAc (2×150 mL). The organic layers were combined, dried over anhydrous Na2SO4, filtered, and concentrated to provide the crude product which was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=50:1-10:1) to obtain 4.96 g of the title compound as a colorless oil. Yield: 55%.

Workup

  1. extractionextracted with EtOAc (2×150 mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto provide the crude product which
  6. customwas purified by column chromatography (silica gel, petroleum ether:ethyl acetate=50:1-10:1)

Sources & evidence

ORD record
ord-d86e1bba4453432aae551fe2cbecd7fa
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

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