Sodium Hydroxide → Bis(4-chlorophenyl)acetaldehyde

HRID 888581Notes

Reaction equation

HRID 888581 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)[CH2:31][OH:32])=[CH:26][CH:25]=1.[OH-].[Na+]>ClCCl>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]([C:33]2[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=2)[CH:31]=[O:32])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 175334-Chloro-beta-(4-chlorophenyl)benzeneethanolHCID 159087Triacetoxyperiodinane

Product 1

HCID 167694Bis(4-chlorophenyl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (3.17 g, 7.49 mmol) was added to a solution of 2,2-Bis-(4-chloro-phenyl)-ethanol in dichloromethane (40 ml). The reaction mixture was stirred at room temperature for 17 hours under nitrogen, 2N NaOH added (15 ml) and the organic layer was separated, dried (MgSO4), filtered and concentrated to afford the title compounds which was used in the next step without further purification. LC/MS: (PS-B3) Rt 3.62 [M+H]+ 262.91.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6657d576ba2442768a506b821e2fd45f
Source dataset
uspto-grants-2012_08
Patent number
US08247576B2

Reaction notes

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