4-Chloro-2-methylbenzoic acid → 4-Chloro-2-methylbenzyl Alcohol

HRID 1192363Notes

Reaction equation

HRID 1192363 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([CH3:11])[CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[C:4]([CH3:11])[CH:3]=1

Participants

4

Reactant 2

HCID 3482694-Chloro-2-methylbenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 27576694-Chloro-2-methylbenzyl AlcoholYield 102.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture containing 4-Chloro-2-methyl-benzoic acid (4 g, 23 mmol) and LiAlH4 (890 mg, 23.5 mmol) in 250 mL of THF under a nitrogen atmosphere was allowed to stir at room temperature for 2 hours. The reaction was quenched with sodium sulfate decahydrate. The mixture was filtered through a pad of Celite and the filter cake washed with THF. The filtrate was concentrated under reduced pressure. Purification of the residue via biotage eluting with 30% ethyl acetate/hexanes gave (4-Chloro-2-methyl-phenyl)-methanol (3.70 g, 100%) as a colorless oil. 1H NMR (CDCl3, 400 MHz) δ 7.30-7.25 (1H, m), 7.18-7.14 (2H, m), 4.66 (2H, d, J 5.8 Hz), 2.32 (3H, s.)

Workup

  1. customThe reaction was quenched with sodium sulfate decahydrate
  2. filtrationThe mixture was filtered through a pad of Celite
  3. washthe filter cake washed with THF
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customPurification of the residue via biotage
  6. washeluting with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-c73712b7e0464a52951d2427d863c41c
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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