Peracetic Acid → 6-Hydroxy-7,7-dimethylcaprylic acid

HRID 435561Notes

Reaction equation

HRID 435561 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:11])(C)(C)C.[C:12]([O-:15])(=[O:14])[CH3:13].[Na+].[C:17](OO)(=O)C>C(Cl)Cl>[OH:11][CH:6]([C:5]([CH3:1])([CH3:10])[CH3:17])[CH2:7][CH2:8][CH2:9][CH2:13][C:12]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 6585Peracetic AcidHCID 1026812-tert-ButylcyclohexanoneHCID 517045Sodium Acetate

Product 1

HCID 214555416-Hydroxy-7,7-dimethylcaprylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The a 3-liter round-bottomed flask provided with a stirrer , thermometer, condenser and dropping funnel, there are added 353 g (2.3 mol) of 2-tert. butyl-cyclohexanone 14 g of anhydrous sodium acetate and 1.17 liters of methylene chloride. 370 g of ca. 40% peracetic acid are added at room temperature while cooling. The mixture is held first at room temperature for 20 hours with stirring and then for a further 48 hours under reflux temperature. After cooling, the mixture is poured on to ice, the layers are separated and the organic layer washed with an iron sulphate solution and then with water until a neutral reaction is obtained. The solvent is distilled off and the crude lactone distilled, there being obtained 274 g (70.3%) of the Σ-lactone of 6-hydroxy-7,7-dimethylcaprylic acid of boiling point 134° C/12 mm Hg; melting point 54°-58° C.

Workup

  1. customThe a 3-liter round-bottomed flask provided with a stirrer
  2. customthermometer, condenser and dropping
  3. temperaturewhile cooling
  4. temperaturefor a further 48 hours under reflux temperature
  5. temperatureAfter cooling
  6. additionthe mixture is poured on to ice
  7. customthe layers are separated
  8. washthe organic layer washed with an iron sulphate solution
  9. customwith water until a neutral reaction
  10. customis obtained
  11. distillationThe solvent is distilled off
  12. distillationthe crude lactone distilled

Sources & evidence

ORD record
ord-8963992a91fd4c0eb99e859ec944fb9e
Source dataset
uspto-grants-1977_02
Patent number
US04006109

Reaction notes

Loading…