Hydrochloric Acid → (2-Methanesulfonylphenyl)methanol

HRID 1642616Notes

Reaction equation

HRID 1642616 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([CH3:13])(=[O:12])=[O:11].[Li+].[BH4-].Cl>C1COCC1>[CH3:13][S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][OH:2])(=[O:11])=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2763931Methyl 2-(methanesulfonyl)benzoateHCID 4148881Lithium borohydride2×

Product 1

HCID 22050773(2-Methanesulfonylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methanesulfonylbenzoic acid methyl ester (1.5 g, 7 mmol) in THF (20 mL) is added LiBH4 (616 mg, 30 mmol) and the mixture is stirred at ambient temperature for 14 h. Additional LiBH4 (310 mg, 15 mmol) is added and the mixture is heated at 65° C. for 45 min. Then under ice cooling, 1N HCl solution is added to quench the excess of LiBH4 before EtOAc is added. The organic layer is washed with brine (2×) and water (1×), dried with MgSO4, and concentrated to give the title compound.

Workup

  1. temperaturethe mixture is heated at 65° C. for 45 min
  2. customto quench the excess of LiBH4 before EtOAc
  3. additionis added
  4. washThe organic layer is washed with brine (2×) and water (1×)
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-59f244cf385f488ba5fbbc57ddc7605a
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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