Peracetic Acid → HCID 20276861, compound

HRID 1105965Notes

Reaction equation

HRID 1105965 reaction equation
[CH2:1]([CH:9]1C[CH2:13][CH2:12][CH2:11][C:10]1=O)[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:8].[C:16](=[O:19])([O-:18])[O-].[Na+].[Na+].C(OO)(=[O:24])C>C(Cl)CCl>[CH2:1]([CH:2]1[O:24][C:3](=[O:8])[CH2:4][CH2:5][CH2:6][CH2:7]1)[CH:9]1[O:18][C:16](=[O:19])[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 6585Peracetic AcidHCID 10340Sodium CarbonateHCID 37551872,2'-methanediyldicyclohexanone

Product 1

HCID 20276861HCID 20276861, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a mixture comprising 20.8 g of 2,2'-methylenebiscyclohexanone and 50 g of powdered anhydrous sodium carbonate, 100 ml of ethylene dichloride was added with stirring. To the resulting solution, a mixture comprising 47.5 g of 40% peracetic acid and 50 ml of ethylene dichloride was added dropwise at 20°-25° C. over a period of about 2 hours. Following stirring for another 3 hours, the reaction mixture was washed first with water, then with a saturated Mohr's salt solution to decompose unreacted peracetic acid, and extracted with ether. The extract was washed with 2% aqueous sodium carbonate once, then washed with saturated aqueous sodium chloride, and the organic phase was dried over anhydrous magnesium sulfate. Concentration of the dried product gave 20.5 g of crude 6,6'-methylenebis-(6-hexanolide). Recrystallizing the crude product from isopropyl ether gave 19.0 g (yield: 79%) of a white crystal of 6,6'-methylenebis-(6-hexanolide) melting at 108°-109° C.

Workup

  1. stirringFollowing stirring for another 3 hours
  2. washthe reaction mixture was washed first with water
  3. extractionextracted with ether
  4. washThe extract was washed with 2% aqueous sodium carbonate once
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialthe organic phase was dried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-3fa4460a0e274e459636648819a6492a
Source dataset
uspto-grants-1982_01
Patent number
US04310685

Reaction notes

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