Acetic Acid → HCID 23330250, compound

HRID 224755Notes

Reaction equation

HRID 224755 reaction equation
[Cl:1][C:2]([Cl:12])([Cl:11])[CH2:3][CH:4]1[C:7]([CH3:9])([CH3:8])[CH2:6][C:5]1=O.[C:13]([OH:16])(=[O:15])C.[OH:17]O>[Fe](Cl)(Cl)Cl.O>[CH3:9][C:7]([CH3:8])([CH:4]([OH:17])[CH2:3][C:2]([Cl:1])([Cl:11])[Cl:12])[CH2:6][CH2:5][C:13]([OH:16])=[O:15]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 23330246HCID 23330246, compound

Product 1

HCID 23330250HCID 23330250, compound

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

15.3 g (0.067 mol) of 2-(2',2',2'-trichloroethyl)-3,3-dimethylcyclobutanone, 75 ml of glacial acetic acid and 7.6 g of a 30% aqueous H2O2 solution are placed together and stirred at 35° C. for 3.5 hours. The mixture is then vigorously stirred up with water containing iron(III)chloride until no further peroxide is detectable. The resulting mixture is extracted with n-hexane. The extract is dried over magnesium sulphate and concentrated by evaporation. The residue (13.4 g) is distilled to yield the lactone of 3,3-dimethyl-4-hydroxy-6,6,6-trichlorohexanecarboxylic acid as a clear liquid; b.p. 108°-111° C./0.3 mm Hg.

Workup

  1. extractionThe resulting mixture is extracted with n-hexane
  2. dry with materialThe extract is dried over magnesium sulphate
  3. concentrationconcentrated by evaporation
  4. distillationThe residue (13.4 g) is distilled

Sources & evidence

ORD record
ord-3dc9c42f0a4d42aba7f3ad22092ad172
Source dataset
uspto-grants-1980_11
Patent number
US04234517

Reaction notes

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