Nonanoic acid, 9-hydroxy-, methyl ester → Methyl 9-oxononanoate

HRID 1263948Notes

Reaction equation

HRID 1263948 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[O:12]

Participants

4

Reactant 2

HCID 292983Nonanoic acid, 9-hydroxy-, methyl esterHCID 2724130Cornforth reagent

Product 1

HCID 74732Methyl 9-oxononanoateYield 72.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9-Hydroxy-nonanoic acid methyl ester (7 g) in dichloromethane was treated with pyridinium dichromate (35 g) and stirred at room temperature for 12 hours. The pyridinium dichromate was filtered, and the organic filtrate was washed by water. Hexane (3× volume) was added to the solution, and organic layer was collected and dried to obtain the crude product. The product was purified by Si gel column chromatography to yield ˜5 g of product.

Workup

  1. filtrationThe pyridinium dichromate was filtered
  2. washthe organic filtrate was washed by water
  3. additionHexane (3× volume) was added to the solution, and organic layer
  4. customwas collected
  5. customdried
  6. customto obtain the crude product
  7. customThe product was purified by Si gel column chromatography

Sources & evidence

ORD record
ord-241ee46be1484aa39eb63e40b628ea8c
Source dataset
uspto-grants-2003_04
Patent number
US06541506B1

Reaction notes

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