2,4'-Dichlorobenzophenone → (2-Chlorophenyl)(4-chlorophenyl)methanol

HRID 1785632

Reaction equation

HRID 1785632 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)=[O:5].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH:4]([OH:5])[C:6]1[CH:7]=[CH:8][C:9]([Cl:12])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 665582,4'-DichlorobenzophenoneHCID 4311764Sodium borohydride

Product 1

HCID 247332(2-Chlorophenyl)(4-chlorophenyl)methanolYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2,4′-dichlorobenzophenone (239 mmol) in methanol (400 mL) was added sodium borohydride (119 mmol) portionwise at 0° C. Reaction mixture was warmed to room temperature and stirred for 1 hour, then quenched with water and the methanol was removed under reduced pressure. The residue was diluted with dichloromethane (400 mL) and washed with water and brine, dried (MgSO4) and concentrated in vacuo to yield the product as an orange oil (47.1 g, 78%).

Workup

  1. customReaction mixture
  2. customquenched with water
  3. customthe methanol was removed under reduced pressure
  4. additionThe residue was diluted with dichloromethane (400 mL)
  5. washwashed with water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0a11525eb48d4e06a5e6cf67c09aa1bb
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Linked notes

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