3-(3-Chlorophenyl)prop-2-enoic acid → 3-(3-Chlorophenyl)propan-1-ol

HRID 890750Notes

Reaction equation

HRID 890750 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=1)[CH:11]=[CH:12][C:13](O)=[O:14]>C1COCC1>[Cl:7][C:8]1[CH:9]=[C:10]([CH2:11][CH2:12][CH2:13][OH:14])[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 746313-(3-Chlorophenyl)prop-2-enoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 99896673-(3-Chlorophenyl)propan-1-olYield 110.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A slurry of lithium aluminum hydride (2.08 g, 54.7 mmol) in THF (100 mL) was cooled to −78° C. A solution of 3-chlorocinnamic acid (5.00 g, 27.4 mmol) in THF (25 mL) was added dropwise. The cold bath was removed and the mixture was warmed to room temperature. After 6 h, the reaction was quenched by addition of sodium sulfate decahydrate and the mixture was stirred overnight. The solids were removed by filtration with the aid of EtOAc and the organic solution was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to yield 3-(3-chloro-phenyl)-propan-1-ol (5.17 g) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.30–7.07 (m, 4H), 5.06 (bs, 1H), 3.67 (m, 2H), 2.69 (m, 2H), 1.89 (m, 2H).

Workup

  1. customThe cold bath was removed
  2. customthe reaction was quenched by addition of sodium sulfate decahydrate
  3. customThe solids were removed by filtration with the aid of EtOAc
  4. washthe organic solution was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f6000a3dbb2f461ab6ecc06a7ca64655
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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