Triethylamine → 2.5-Di-[(methanesulfonyl)oxy]benzaldehyde

HRID 412162

Reaction equation

HRID 412162 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>ClCCl>[CH3:18][S:19]([O:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][S:19]([CH3:18])(=[O:21])=[O:20])=[CH:6][C:3]=1[CH:4]=[O:5])(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 709492,5-Dihydroxybenzaldehyde

Product 1

HCID 185361862.5-Di-[(methanesulfonyl)oxy]benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,5-dihydroxybenzaldehyde (8.22 g, 59.5 mmol) in 100 mL of dichloromethane at 0° C. was added triethylamine (24.8 mL, 178 mmol), followed by dropwise addition of methanesulfonyl chloride (10.1 mL, 130 mmol). After 30 minutes, the solution was concentrated in vacuo, then partitioned between EtOAc and saturated NaHCO3 solution. The organic layer was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was isolated as a brown oil which was used without further purification.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. custompartitioned between EtOAc and saturated NaHCO3 solution
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was isolated as a brown oil which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-5623e8b1669c443d8e97930d5d019eb5
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Linked notes

Loading…