Water → (3-Chloro-2-methylphenyl)methanol

HRID 1042349Notes

Reaction equation

HRID 1042349 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:11]=1[CH3:17].O>C1COCC1>[Cl:16][C:12]1[C:11]([CH3:17])=[C:10]([CH2:9][OH:8])[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5077673Methyl 3-chloro-2-methylbenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 13169022(3-Chloro-2-methylphenyl)methanolYield 103.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LAH (61.00 mL, 1.0 M in THF, 61.00 mmol) was added to a solution of 3-chloro-2-methyl-benzoic acid methyl ester (4.50 g, 24.40 mmol) in THF at 0° C. The reaction mixture was stirred for 1 hour, water was added to quench the reaction. The aqueous layer was extracted with Et2O (3×150 mL), and the combined organic phases were washed with brine (1×150 mL) and dried over MgSO4. Purification by column chromatography using hex:EtOAc (4:1) as the eluant afforded 3.97 g of the title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3.) δ 1.94 (br s, 1H), 2.36 (s, 3H), 4.67 (br s, 2H), 7.11 (t, J=7.765 Hz, 1H), 7.245 (d, J=7.03 Hz, 1H), 7.30 (d, J=7.91 Hz, 1H).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe aqueous layer was extracted with Et2O (3×150 mL)
  4. washthe combined organic phases were washed with brine (1×150 mL)
  5. dry with materialdried over MgSO4
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-d4d8729ed4114d8ebe420d370e76668a
Source dataset
uspto-grants-2013_10
Patent number
US08557853B2

Reaction notes

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