Water → HCID 86687812, compound

HRID 716503Notes

Reaction equation

HRID 716503 reaction equation
C([O-])(O)=O.[Na+].O.[CH:7]1([CH2:12][CH:13]([CH3:17])[CH2:14][CH2:15][OH:16])[CH2:11][CH2:10][CH2:9][CH2:8]1.[O-]Cl.[Na+]>[K+].[Br-].CC1(C)N([O])C(C)(C)CCC1.C1(C)C=CC=CC=1>[CH:7]1([CH2:12][CH:13]([CH3:17])[CH2:14][CH:15]=[O:16])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

8

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 23665760Sodium HypochloriteHCID 66584124HCID 66584124, compound

Product 1

HCID 86687812HCID 86687812, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 253877Potassium BromideCatalystHCID 2724126TempoCatalystHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

KBr (0.6 g, 0.005 mol) and NaHCO3 (6.4 g, 0.076 mol) and 0.8 g (0.00566 mols) 2,2,6,6-Tetramethylpiperidine-1-oxyl (TEMPO) were mixed together with water (60 ml), toluene (250 g) and 4-cyclopentyl-3-methylbutan-1-ol (70.2 g 0.45 mol, purity:98%) the reaction temperature maintain 0° C. with continuous stirring. NaOCl (12% w/w aqueous 426.8 g, 0.745 mol) was added to the reaction mass over 2 h. Stirring was continued for another 12 h. The aqueous phase was removed, organic phase was washed with a solution of NaHCO3 and then with water. The organic phase thus obtained was concentrated and crude product purified by fractional distillation to provide 4-cyclopentyl-3-methylbutanal (41.58 g, yield: 60%, GC purity: 97%)

Workup

  1. customThe aqueous phase was removed
  2. washorganic phase was washed with a solution of NaHCO3
  3. customThe organic phase thus obtained
  4. concentrationwas concentrated
  5. distillationcrude product purified by fractional distillation

Sources & evidence

ORD record
ord-4f65b5b9905b44dd85e04ec8944089f7
Source dataset
uspto-grants-2015_11
Patent number
US09187709B2

Reaction notes

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