Vanillin → 4-Formyl-2-methoxyphenyl trifluoromethanesulfonate

HRID 1844524Notes

Reaction equation

HRID 1844524 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].CCN(CC)CC.[O:19](S(C(F)(F)F)(=O)=O)[S:20]([C:23]([F:26])([F:25])[F:24])(=O)=[O:21]>C(Cl)Cl>[F:24][C:23]([F:26])([F:25])[S:20]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11])(=[O:21])=[O:19]

Participants

5

Reactant 3

HCID 1183VanillinHCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 108029624-Formyl-2-methoxyphenyl trifluoromethanesulfonateYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-hydroxy-3-methoxybenzaldehyde (10.0 g, 65.7 mmol) and Et3N (13.0 g, 128.7 mmol) in anhydrous DCM (100 mL) was added Tf2O (28.0 g, 99.2 mmol) dropwise at room temperature and the reaction was stirred for 1 hour. The resulting mixture was quenched with water (100 mL) followed by a standard aqueous/EtOAc workup. The residue was purified by silica gel column chromatography (PE:EtOAc=20:1) to give the product as a colorless oil (17.0 g, yield 91%).

Workup

  1. customThe resulting mixture was quenched with water (100 mL)
  2. customThe residue was purified by silica gel column chromatography (PE:EtOAc=20:1)

Sources & evidence

ORD record
ord-f6bcfde68bea4970a4e34b95aeeabcff
Source dataset
uspto-grants-2015_02
Patent number
US08946434B2

Reaction notes

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