Hydrochloric Acid → Methanesulfonic acid 2-hydroxymethyl-5-methylphenyl ester

HRID 889237Notes

Reaction equation

HRID 889237 reaction equation
CO[C:3](=[O:16])[C:4]1[CH:9]=[C:8](C)[CH:7]=[CH:6][C:5]=1[O:11][S:12]([CH3:15])(=[O:14])=[O:13].[Li+].[BH4-].[CH3:19]O.Cl>C1COCC1.O.CCOC(C)=O>[OH:16][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:19])=[CH:6][C:5]=1[O:11][S:12]([CH3:15])(=[O:13])=[O:14]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4148881Lithium borohydrideHCID 866389792-Methanesulfonyloxy-5-methylbenzoic acid methyl ester

Product 1

HCID 86638980Methanesulfonic acid 2-hydroxymethyl-5-methylphenyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-methanesulfonyloxy-5-methylbenzoic acid methyl ester (15 g, 61.4 mmol) in THF (30 mL) at 0° C. is added portionwise LiBH4 (4.0 g, 184 mmol) and the mixture is stirred for 15 min. Then MeOH (8 mL, 196 mmol) is added dropwise over 30 min. The mixture is stirred under ice cooling for 30 min, then at RT for 18 h. EtOAc is added followed by ice and water. The mixture is acidified slowly with 1N HCl solution and organic phase is separated. The aqueous phase is extracted with EtOAc. The organic phases are combined, and washed with 1N HCl solution, and brine. It is then dried over Na2SO4 and MgSO4, and concentrated to give the title compound as an oil.

Workup

  1. stirringThe mixture is stirred under ice cooling for 30 min
  2. waitat RT for 18 h
  3. customis separated
  4. extractionThe aqueous phase is extracted with EtOAc
  5. washwashed with 1N HCl solution, and brine
  6. dry with materialIt is then dried over Na2SO4 and MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-43bda875ea0e4992ba35cf7b3cdb75c2
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

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