Methyl 4-(7-cyano-3-hydroxymethylheptyl)benzoate → Methyl 4-(7-cyano-3-formylheptyl)benzoate

HRID 1927426Notes

Reaction equation

HRID 1927426 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([CH2:20][OH:21])[CH2:8][CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1)#[N:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([CH:20]=[O:21])[CH2:8][CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1)#[N:2]

Participants

4

Reactant 2

HCID 57831355Methyl 4-(7-cyano-3-hydroxymethylheptyl)benzoateHCID 178418287HCID 178418287, compound

Product 1

HCID 57831357Methyl 4-(7-cyano-3-formylheptyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.23 g (7.71 mmol) of methyl 4-(7-cyano-3-hydroxymethylheptyl)benzoate in 100 ml of dichloromethane is mixed with 1.99 g (9.26 mmol) of pyridinium chlorochromate (PCC) and stirred at room temperature for 6 hours. After conversion is complete, the solvent is concentrated to dryness in vacuo. The resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1→4:1). 1.50 g (9.09 mmol, 68% of theory) of an oil are obtained.

Workup

  1. concentrationthe solvent is concentrated to dryness in vacuo
  2. customThe resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1→4:1)
  3. custom1.50 g (9.09 mmol, 68% of theory) of an oil are obtained

Sources & evidence

ORD record
ord-233ca1d04b054d20927e10d201128595
Source dataset
uspto-grants-2012_05
Patent number
US08183271B2

Reaction notes

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