4-Hydroxybenzaldehyde → 4-Formylphenyl methanesulfonate

HRID 2249580Notes

Reaction equation

HRID 2249580 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:16][S:17](Cl)(=[O:19])=[O:18]>CN(C=O)C.C(OCC)(=O)C>[CH3:16][S:17]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)(=[O:19])=[O:18]

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chloride

Product 1

HCID 144212934-Formylphenyl methanesulfonateYield 25%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-hydroxybenzaldehyde (5.0 gm, 1.0 eq, 40.98 mmol), anhydrous K2CO3 (17 g, 3 eq, 123 mmol), and methanesulfonylchloride (4.76 mL, 1.5 eq, 61.37 mmol) in dry DMF (200 mL) was stirred at RT for 16 h. The reaction mixture was diluted with ethyl acetate (200 mL) and washed with water and brine. Organic layer was dried (Na2SO4), condensed, and the residue obtained was chromatographed using ethyl acetate and hexanes to obtain the title compound as white solid (2.0 g, 25%).

Workup

  1. washwashed with water and brine
  2. customOrganic layer was dried
  3. custom(Na2SO4), condensed
  4. customthe residue obtained
  5. customwas chromatographed

Sources & evidence

ORD record
ord-858ef44fbdcc41a386e9600d04668e03
Source dataset
uspto-grants-2008_01
Patent number
US07314889B2

Reaction notes

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