4-Hydroxybenzaldehyde → HCID 21705009, compound

HRID 1595547Notes

Reaction equation

HRID 1595547 reaction equation
FC(F)(F)S([O:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][S:16]([C:19]([F:22])([F:21])[F:20])(=[O:18])=[O:17])=[CH:11][CH:10]=1)(=O)=O.O[C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[F:20][C:19]([F:22])([F:21])[S:16]([O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][O:6][C:26]2[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=2)=[CH:10][CH:11]=1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 10796Cesium carbonateHCID 21705001HCID 21705001, compound

Product 1

HCID 21705009HCID 21705009, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.85 g (2.11 mmole) of 4-(trifluoromethylsulfonyloxy)phenethyl trifluoromethansulfonate, 0.27 g (2.2 mmole) p-hydroxybenzaldehyde and 0.72 g (2.2 mmole) cesium carbonate in acetonitrile was stirred at room temperature over night. The salts were filtered off and the solvent evaporated in vacuo. Purification by chromatography on silica gel using dichloromethane as eluent gave 0.6 g (yield 75%) of 4-[2-(4-formylphenoxy)ethyl]phenyl trifluoromethanesulfonate.

Workup

  1. filtrationThe salts were filtered off
  2. customthe solvent evaporated in vacuo
  3. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-55ec0263929b40b4b44917f3a6dfb992
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

Loading…