Vanillin → 4-Formyl-2-methoxyphenyl trifluoromethanesulfonate

HRID 924653Notes

Reaction equation

HRID 924653 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-4d2b033d3b9a4bc09d7a13cb1b1fd0f3
Source dataset
uspto-grants-2016_03
Patent number
US09283213B2

Reaction notes

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