Hydrochloric Acid → Methanesulfonic acid 4-hydroxymethyl-phenyl ester

HRID 709445Notes

Reaction equation

HRID 709445 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:6][CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl>C1COCC1>[OH:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10466383Benzoic acid, 4-[(methylsulfonyl)oxy]-, methyl esterHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 85989572Methanesulfonic acid 4-hydroxymethyl-phenyl esterYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Methanesulfonyloxy-benzoic acid methyl ester (330 mg, 1.43 mmol) was dissolved in anhydrous THF (10 mL) and LiAlH4 (109 mg, 2.86 mmol) was added. The resulting suspension was stirred at room temperature until no starting material was left. Excess LiAlH4 was hydrolyzed with aq. HCl (2N) and the remaining suspension was extracted with EtOAc. The organic layer was separated, dried (MgSO4) and evaporated and the remaining crude product was purified by flash chromatography using n-heptane/EtOAc 3:7 as the eluent to afford the title compound as an oil (202 mg, 93%). 1H NMR (400 MHz, CDCl3): δ 7.37-7.40 (d, 2H), 7.23-7.25 (d, 2H), 4.67 (s br, 2H), 3.10 (s, 3H).

Workup

  1. waitwas left
  2. extractionthe remaining suspension was extracted with EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customthe remaining crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-58952f872aec44659fab1d8690531e6a
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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