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

HRID 1913793Notes

Reaction equation

HRID 1913793 reaction equation
[OH:1][CH2:2][CH:3]([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)[CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH:2]([CH:3]([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)[CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)=[O:1]

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

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 is mixed with 13.07 g (60.6 mmol) of pyridinium chlorochromate (PCC) and stirred at room temperature for 12 hours. After conversion is complete, about 60 g of silica gel are added, and the solvent is removed in vacuo to dryness. The residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1→4:1). 14.73 g (41.46 mmol, 82% of theory) of a colourless oil are obtained.

Workup

  1. additionabout 60 g of silica gel are added
  2. customthe solvent is removed in vacuo to dryness
  3. customThe residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1→4:1)
  4. custom14.73 g (41.46 mmol, 82% of theory) of a colourless oil are obtained

Sources & evidence

ORD record
ord-dbdf546216c342d2a997cabcb9c0a8f5
Source dataset
uspto-grants-2013_12
Patent number
US08609727B2

Reaction notes

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