Water → 2-Formylphenyl 4-(trifluoromethyl)benzenesulfonate

HRID 1795102Notes

Reaction equation

HRID 1795102 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH:15](=[O:23])[C:16]1[C:17](=[CH:19][CH:20]=[CH:21][CH:22]=1)[OH:18].O.C(OCC)(=O)C>N1C=CC=CC=1>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[CH:15]=[O:23])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6998SalicylaldehydeHCID 8857Ethyl AcetateHCID 27773994-(Trifluoromethyl)benzenesulfonyl chloride

Product 1

HCID 221856712-Formylphenyl 4-(trifluoromethyl)benzenesulfonateYield 52.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-(trifluoromethyl)benzenesulphonyl chloride (2.4 g, 9.84 mmol) in pyridine (40 mL) is cooled to 0° C. Salicylaldehyde (1.44 g, 11.8 mmol) is added and stirred overnight. Water and ethyl acetate are added to the reaction and shaken. The organic layer is washed with dilute HCl (0.1 N×2), H2O, bicarbonate solution, H2O and dried with sodium sulfate. The organic layer is evaporated to dryness to give a yellow solid, which is recrystallized from ether/hexane to give 2-formylphenyl 4-(trifluoromethyl)benzenesulfonate as a yellow powder (1.70 g, 52%).

Workup

  1. stirringshaken
  2. washThe organic layer is washed with dilute HCl (0.1 N×2), H2O, bicarbonate solution, H2O
  3. dry with materialdried with sodium sulfate
  4. customThe organic layer is evaporated to dryness
  5. customto give a yellow solid, which
  6. customis recrystallized from ether/hexane

Sources & evidence

ORD record
ord-fd21f148b6254d80a3e6df1b59f886b1
Source dataset
uspto-grants-2006_04
Patent number
US07026339B2

Reaction notes

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