Methyl 5-chloro-2-methoxybenzoate → (5-Chloro-2-methoxyphenyl)methanol

HRID 11647Notes

Reaction equation

HRID 11647 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[O:11][CH3:12].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:10][C:8]1[CH:7]=[CH:6][C:5]([O:11][CH3:12])=[C:4]([CH2:3][OH:2])[CH:9]=1

Participants

4

Reactant 2

HCID 118574Methyl 5-chloro-2-methoxybenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 4357585(5-Chloro-2-methoxyphenyl)methanolYield 999.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-chloro-2-methoxy-benzoic acid methyl ester (20 g, 9.97 mmol) in THF (100 mL) at 0° C. was added dropwise a solution of lithium aluminum hydride (210 mL, 210 mmol, 1M soln. in THF). The solution was then warmed to reflux for 2 hours. The reaction was cooled to 0° C. and carefully quenched by the addition of cold water. The mixture was filtered through celite and the filter cake was washed with diethyl ether. The filtrate was washed with saturated aqueous sodium hydrogen carbonate then dried over magnesium sulfate. Concentration in vacuo gave the title compound (17.2 g).

Workup

  1. temperatureThe solution was then warmed
  2. temperatureto reflux for 2 hours
  3. customcarefully quenched by the addition of cold water
  4. filtrationThe mixture was filtered through celite
  5. washthe filter cake was washed with diethyl ether
  6. washThe filtrate was washed with saturated aqueous sodium hydrogen carbonate
  7. dry with materialthen dried over magnesium sulfate
  8. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-cf5034813b064e95bf4b078c69cd9ad9
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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