Methyl 4-(6-cyano-2-hydroxymethylhexyl)benzoate → Methyl 4-(6-cyano-2-formylhexyl)benzoate

HRID 1672701Notes

Reaction equation

HRID 1672701 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([CH2:19][OH:20])[CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=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:19]=[O:20])[CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1)#[N:2]

Participants

4

Reactant 2

HCID 57864355Methyl 4-(6-cyano-2-hydroxymethylhexyl)benzoateHCID 178418287HCID 178418287, compound

Product 1

HCID 57864395Methyl 4-(6-cyano-2-formylhexyl)benzoateYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.8 g (13.80 mmol) of methyl 4-(6-cyano-2-hydroxymethylhexyl)benzoate from Example 117A in 250 ml of dichloromethane is mixed with 3.57 g (16.56 mmol) of pyridinium chlorochromate (PCC) and stirred at room temperature for 12 hours. After conversion is complete, 10 g of silica gel are added and the solvent is cautiously concentrated to dryness in vacuo. The resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1:1). 3.49 g (92% yield) are obtained as a colorless solid.

Workup

  1. addition10 g of silica gel are added
  2. concentrationthe solvent is cautiously concentrated to dryness in vacuo
  3. customThe resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1:1)
  4. custom3.49 g (92% yield) are obtained as a colorless solid

Sources & evidence

ORD record
ord-2443aba3a8574e0193fcabe5a0758dc1
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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