Vanillin → 4-Formyl-2-methoxyphenyl trifluoromethanesulfonate

HRID 471857Notes

Reaction equation

HRID 471857 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 trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-hydroxy-3-(methoxy)benzaldehyde (0.760 g; 5.00 mmol) and Et3N (1.39 mL; 10.0 mmol) in anhyd CH2Cl2 (10 mL) at 0° C. was added Tf2O (0.92 mL; 5.5 mmol), dropwise over 2 min. The mixture was allowed to warm slowly to room temperature (overnight), diluted with CH2Cl2, washed (water, brine), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 4.01 (s, 3H), 7.42 (d, J=8.2 Hz, 1H), 7.52 (dd, J=8.2, 1.8 Hz, 1H), 7.57 (d, J=1.7 Hz, 1H), 9.99 (s, 1H).

Workup

  1. washwashed (water, brine)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-52c444bb32904444bf8ee43c42252c9a
Source dataset
uspto-grants-2014_01
Patent number
US08633175B2

Reaction notes

Loading…