4,4'-Dichlorobenzophenone → 1-Chloro-4-[(4-chlorophenyl)-dimethoxymethyl]benzene

HRID 406962Notes

Reaction equation

HRID 406962 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH:17](OC)(OC)[O:18]C.Cl(O)(=O)(=O)=O.[C:29]([O-])(O)=O.[Na+]>CO.C(OCC)(=O)C>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)([O:18][CH3:17])[O:7][CH3:29])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 70344,4'-DichlorobenzophenoneHCID 9005Trimethyl orthoformateHCID 24247Perchloric AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 116523071-Chloro-4-[(4-chlorophenyl)-dimethoxymethyl]benzene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
27.5 °C

Procedure

In a round bottom flask, (2 g) 4,4′-dichlorobenzophenone in 4 ml methanol was taken. (1.75 ml) (2 equiv.) tri-methyl orthoformate was added into the reaction mixture and stirred at 25-30° C. Then 0.04 ml perchloric acid (as a catalyst) was added and refluxed for 7.5 hrs. After completion of the reaction ethyl acetate and NaHCO3 solution were added and stirred for 10 min. Then layers were separated and washed the organic layer with water. Dry it over sodium sulfate. Concentrate it on rotavapor to obtain yellow colored liquid product

Workup

  1. temperaturerefluxed for 7.5 hrs
  2. additionwere added
  3. stirringstirred for 10 min
  4. customThen layers were separated
  5. washwashed the organic layer with water
  6. dry with materialDry it over sodium sulfate
  7. concentrationConcentrate it on rotavapor
  8. customto obtain yellow colored liquid product

Sources & evidence

ORD record
ord-6d5063829bc74a3e90895baa3dc9ac0d
Source dataset
uspto-grants-2014_06
Patent number
US08754207B2

Reaction notes

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