Dimethyl Sulfoxide → 1,3-Bis(4-formylphenoxy)-5-chlorobenzene

HRID 263530

Reaction equation

HRID 263530 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:12]=[C:13]([OH:18])[CH:14]=[C:15]([CH:17]=1)[OH:16].[C:19](=[O:22])([O-])[O-].[K+].[K+].CS(C)=O>C(OCC)(=O)C.O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:16][C:15]2[CH:17]=[C:11]([Cl:10])[CH:12]=[C:13]([O:18][C:2]3[CH:9]=[CH:8][C:5]([CH:19]=[O:22])=[CH:4][CH:3]=3)[CH:14]=2)=[CH:3][CH:4]=1)=[O:7]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 945541,3-Benzenediol, 5-chloro-

Product 1

HCID 190384981,3-Bis(4-formylphenoxy)-5-chlorobenzeneYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

p-Fluorobenzaldehyde (7.7 g), 5.9 g of 5-chlororesorcinol and 12.3 g of anhydrous potassium carbonate were added to 50 ml of dimethyl sulfoxide and stirred for 12 hours at 100° C. After completion of the reaction, 100 ml of water and 200 ml of ethyl acetate were added to carry out phase separation. After three times of washing with 50 ml of 10% sodium chloride aqueous solution and subsequent drying over anhydrous magnesium sulfate, the solvent was evaporated. The resulting oily material was subjected to silica gel column chromatography (hexane:ethyl acetate (7:1)) to obtain 3.5 g of 1,3-bis(4-formylphenoxy)-5-chlorobenzene.

Workup

  1. additionwere added
  2. customphase separation
  3. washAfter three times of washing with 50 ml of 10% sodium chloride aqueous solution
  4. dry with materialsubsequent drying over anhydrous magnesium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e01cc9ccd90348c2825383fc5f394d19
Source dataset
uspto-grants-1997_07
Patent number
US05643931

Linked notes

Loading…