2,4-Dichlorobenzaldehyde → 2,4,4'-Trichlorobenzhydrol

HRID 1785628Notes

Reaction equation

HRID 1785628 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([Mg]Br)=[CH:14][CH:13]=1>C(OCC)C>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]([OH:5])[C:15]1[CH:16]=[CH:17][C:12]([Cl:11])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 134042,4-DichlorobenzaldehydeHCID 178478191HCID 178478191, compound

Product 1

HCID 225654352,4,4'-TrichlorobenzhydrolYield 73%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 2,4-dichlorobenzaldehyde (286 mmol) in diethyl ether (500 mL) was added 4-chlorophenylmagnesium bromide (1.0 M in diethyl ether, 286 mmol) dropwise at 0° C. over a period of 1 hour. The reaction was allowed to warm to ambient temperature, and stirred for 3 h. The reaction mixture was quenched with saturated ammonium chloride solution (500 mL) and extracted with diethyl ether (2×500 mL), the extracts were washed with water and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by trituration with iso-hexane (500 mL) to yield the product as a white solid (60.0 g, 73%).

Workup

  1. customThe reaction mixture was quenched with saturated ammonium chloride solution (500 mL)
  2. extractionextracted with diethyl ether (2×500 mL)
  3. washthe extracts were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by trituration with iso-hexane (500 mL)

Sources & evidence

ORD record
ord-ff8c0eb5ff914c889b612fb608cbb1c6
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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