Sodium Hydroxide → Bis(4-chlorophenyl)acetaldehyde

HRID 924713Notes

Reaction equation

HRID 924713 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-ae0a05bf52cb41c0a68893d43a4499a4
Source dataset
uspto-grants-2016_03
Patent number
US09283226B2

Reaction notes

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