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

HRID 1958010Notes

Reaction equation

HRID 1958010 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[C:9]([CH3:18])=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11](OC)=[O:12].O.[OH-].[Na+]>O1CCCC1>[Cl:7][C:8]1[C:9]([CH3:18])=[C:10]([CH2:11][OH:12])[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 5077673Methyl 3-chloro-2-methylbenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 13169022(3-Chloro-2-methylphenyl)methanolYield 94.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of lithium aluminium hydride (29.8 mL, 29.8 mmol) in THF was cooled to 0° C., and a solution of methyl 3-chloro-2-methylbenzoate (2.5 g, 13.54 mmol) in Tetrahydrofuran (THF) (20 mL) was added dropwise. The mixture was stirred at 0° C. for half hour, warmed up to RT gradually, and stirred at RT for 2 hours. Water and 6N NaOH (4 ml) were added to quench the reaction. The mixture was filtered and the filtrate was concentrated to afford the crude product as a white solid (2.0 g, 94%). 1H NMR (400 MHz, CDCl3) δppm 7.30˜7.35 (m, 2H), 7.16 (m, 1H), 4.74 (s, 2H), 2.40 (s, 3H).

Workup

  1. temperaturewarmed up to RT gradually
  2. stirringstirred at RT for 2 hours
  3. customto quench
  4. customthe reaction
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-92c04c209d7144fe87e0610ba4b4a490
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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