Water → (3-Methanesulfonylphenyl)methanol

HRID 1515084Notes

Reaction equation

HRID 1515084 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](O)=[O:9])(=[O:4])=[O:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH2:8][OH:9])[CH:11]=[CH:12][CH:13]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 2203803-Methanesulfonylbenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 23549738(3-Methanesulfonylphenyl)methanolYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-(Methylsulfonyl)benzoic acid (540 mg, 2.70 mmol) was dissolved in tetrahydrofuran (40 mL), and the resulting solution was cooled to 0° C. Then, lithium aluminum hydride (102 mg, 2.70 mmol) was added thereto, and the temperature of the resulting mixture was raised to room temperature, and the mixture was stirred for 3 hours. Water was added to the reaction solution, and the organic matter was extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution, then dried over anhydrous magnesium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby a crude product was obtained. This crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 70:30 (v/v)), whereby the objective title compound was obtained as a colorless oily substance (257 mg, yield: 51%).

Workup

  1. temperaturethe temperature of the resulting mixture was raised to room temperature
  2. extractionthe organic matter was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated sodium chloride solution, then dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. distillationThen, the solvent was distilled off under reduced pressure, whereby a crude product
  7. customwas obtained
  8. customThis crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 70:30 (v/v)), whereby the objective title compound
  9. customwas obtained as a colorless oily substance (257 mg, yield: 51%)

Sources & evidence

ORD record
ord-f49770080d1040e28f6776ff39873283
Source dataset
uspto-grants-2012_07
Patent number
US08222281B2

Reaction notes

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