Dimethyl 4,4'-[3-(hydroxymethyl)pentane-1,5-diyl]dibenzoate → Dimethyl 4,4'-(3-formylpentane-1,5-diyl)dibenzoate

HRID 1512200Notes

Reaction equation

HRID 1512200 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[OH:12][CH2:13][CH:14]([CH2:27][CH2:28][C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=1)[CH2:15][CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1>ClCCl>[CH:13]([CH:14]([CH2:27][CH2:28][C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=1)[CH2:15][CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1)=[O:12]

Participants

4

Reactant 2

HCID 59397501Dimethyl 4,4'-[3-(hydroxymethyl)pentane-1,5-diyl]dibenzoateHCID 178418287HCID 178418287, compound

Product 1

HCID 59397497Dimethyl 4,4'-(3-formylpentane-1,5-diyl)dibenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.1 g (28.3 mmol) of pyridinium chlorochromate (PCC) are added to a solution of 8.73 g (23.6 mmol) of dimethyl 4,4′-[3-(hydroxymethyl)pentane-1,5-diyl]dibenzoate in 280 ml of dichloromethane, and the mixture is stirred at room temperature for 12 h. After the reaction has gone to completion, about 10 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 4:1). This gives 7.08 g (19.22 mmol, 81.5% 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 4:1)

Sources & evidence

ORD record
ord-38d26006514a4bf3838c0e8dc783d94a
Source dataset
uspto-grants-2012_07
Patent number
US08217063B2

Reaction notes

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