Hydrochloric Acid → (2-Chlorophenyl)(4-chlorophenyl)methanol

HRID 28263

Reaction equation

HRID 28263 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][CH:4]=1.[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]=[O:14].Cl>O.CCOCC>[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]([OH:14])[C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 69962-ChlorobenzaldehydeHCID 7806p-Bromochlorobenzene2×HCID 5462224Magnesium

Product 1

HCID 247332(2-Chlorophenyl)(4-chlorophenyl)methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To 12.7 g. (0.52 moles) of magnesium turnings in 200 ml. of anhydrous ether is added 10.0 g. (0.052 moles) of p-bromochlorobenzene, and the mixture is warmed to reflux. When the Grignard reaction begins, the heat is removed and 80.0 g. (0.47 moles) of additional p-bromochlorobenzene in 80 ml. of ether is added dropwise as the refluxing continues. When the addition is completed, the reaction is heated at reflux for 2 hours, cooled, and 73.4 g. (0.52 moles) of o-chlorobenzaldehyde are slowly added. The reaction is refluxed for 2 hours, cooled and poured into iced water. The resulting mixture is made acidic with hydrochloric acid, and the organic phase is separated. The aqueous layer is extracted with ether, and the extract is added to the organic phase. This solution is washed with water, dried over anhydrous magnesium sulfate and concentrated to give an oily solid. The material is crystallized from petroleum ether to give 109.4 g. (83%) of the product, mp 68°-70°.

Workup

  1. customWhen the Grignard reaction
  2. customthe heat is removed
  3. additionWhen the addition
  4. temperaturethe reaction is heated
  5. temperatureat reflux for 2 hours
  6. temperaturecooled
  7. temperatureThe reaction is refluxed for 2 hours
  8. temperaturecooled
  9. customthe organic phase is separated
  10. extractionThe aqueous layer is extracted with ether
  11. additionthe extract is added to the organic phase
  12. washThis solution is washed with water
  13. dry with materialdried over anhydrous magnesium sulfate
  14. concentrationconcentrated
  15. customto give an oily solid
  16. customThe material is crystallized from petroleum ether
  17. customto give 109.4 g

Sources & evidence

ORD record
ord-d1fb74da1fe1496a9557c93116c7aab5
Source dataset
uspto-grants-1980_09
Patent number
US04225723

Linked notes

Loading…