Dimethyl 4,4'-[2-(hydroxymethyl)butane-1,4-diyl]dibenzoate → Dimethyl 4,4'-(2-formylbutane-1,4-diyl)dibenzoate

HRID 1512206Notes

Reaction equation

HRID 1512206 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[OH:12][CH2:13][CH:14]([CH2:26][CH2:27][C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1)[CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1>ClCCl>[CH:13]([CH:14]([CH2:26][CH2:27][C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1)[CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)=[O:12]

Participants

4

Reactant 2

HCID 59180517Dimethyl 4,4'-[2-(hydroxymethyl)butane-1,4-diyl]dibenzoateHCID 178418287HCID 178418287, compound

Product 1

HCID 59180526Dimethyl 4,4'-(2-formylbutane-1,4-diyl)dibenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

13.07 g (60.6 mmol) of pyridinium chlorochromate (PCC) are added to a solution of 18.02 g (50.5 mmol) of dimethyl 4,4′-[2-(hydroxymethyl)butane-1,4-diyl]dibenzoate in 350 ml of dichloromethane, and the mixture is stirred at room temperature for 12 hours. After the reaction has gone to completion, about 60 g of silica gel are added and the solvent is removed to dryness under reduced pressure. The residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1→4:1). This gives 14.73 g (41.46 mmol, 82% of theory) of a colorless oil.

Workup

  1. additionare added
  2. customthe solvent is removed to dryness under reduced pressure
  3. customThe residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1→4:1)

Sources & evidence

ORD record
ord-2033b08280c14d22b33b87e3d9cf7cdf
Source dataset
uspto-grants-2012_07
Patent number
US08217063B2

Reaction notes

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