Water → HCID 86687810, compound

HRID 716494Notes

Reaction equation

HRID 716494 reaction equation
C([O-])(O)=O.[Na+].O.[CH:7]1([CH2:13][CH:14]([CH3:18])[CH2:15][CH2:16][OH:17])[CH2:12][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([CH2:13][CH:14]([CH3:18])[CH2:15][CH:16]=[O:17])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

8

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 15054999HCID 15054999, compoundHCID 23665760Sodium Hypochlorite

Product 1

HCID 86687810HCID 86687810, compoundYield 45%

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-(cyclohex-1-yl)-3-methyl butan-1-ol (96 g 0.564 mol, purity: 99% sum of the isomers) the reaction temperature maintain 0° C. with continuous stirring. NaOCl (13% 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-(Cyclohex-1-yl)-3-methylbutanal (42.63 g, yield: 45%, GC purity: 95%).

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-2044040f4ca846679d5cab3613ed5366
Source dataset
uspto-grants-2015_11
Patent number
US09187709B2

Reaction notes

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