Isovanillin → 4-Methoxy-3-[(methylsulfonyl)oxy]benzaldehyde

HRID 1776576Notes

Reaction equation

HRID 1776576 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[CH3:12][S:13](Cl)(=[O:15])=[O:14]>C(Cl)Cl>[CH3:12][S:13]([O:1][C:2]1[CH:3]=[C:4]([CH:5]=[O:6])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 12127IsovanillinHCID 31297Methanesulfonyl chloride

Product 1

HCID 588275424-Methoxy-3-[(methylsulfonyl)oxy]benzaldehydeYield 87.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-hydroxy-4-methoxybenzaldehyde (2.5 g, 16.4 mmol) was dissolved in DCM (50 ml), then methanesulfonyl chloride (2 g, 17.5 mmol) and TEA (4 ml, 28.6 mmol) were added, and the reaction was stirred at RT for 12 hours. DCM was evaporated, and the mixture was dissolved in ethyl acetate and extracted with HCl 1M, dried over Na2SO4 and evaporated under vacuum to yield 3.3 g of the desired product. (Yield: 87%).

Workup

  1. customDCM was evaporated
  2. dissolutionthe mixture was dissolved in ethyl acetate
  3. extractionextracted with HCl 1M
  4. dry with materialdried over Na2SO4
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-b66228e8e22b4d1dbe6134cf4370350f
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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