Peracetic Acid → (2-Ethyl-1,7-dioxaspiro[4.5]decan-2-yl)methanol

HRID 647742Notes

Reaction equation

HRID 647742 reaction equation
[CH2:1]=[C:2]([CH2:12][CH3:13])[CH2:3][CH2:4][C:5]1([OH:11])[CH2:10][CH2:9][CH2:8][O:7][CH2:6]1.C(OO)(=[O:16])C.C([O-])(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[CH2:12]([C:2]1([CH2:1][OH:16])[CH2:3][CH2:4][C:5]2([CH2:10][CH2:9][CH2:8][O:7][CH2:6]2)[O:11]1)[CH3:13]

Participants

6

Reactant 3

HCID 6585Peracetic AcidHCID 517045Sodium AcetateHCID 132371553-(3-Methylidenepentyl)oxan-3-ol

Product 1

HCID 13237156(2-Ethyl-1,7-dioxaspiro[4.5]decan-2-yl)methanolYield 91.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5.75 g of tetrahydro-3-(3-methylenepentyl)-2H-pyran-3-ol in 40 ml methylene chloride was added in four portions, 6.5 g of 40% peracetic acid in acetic acid containing 145 mg of anhydrous sodium acetate. A temperature increase from 20° C. to 37° C. resulted. The resulting solution was refluxed for 1 hour and stirred at ambient temperature for 4 hours. The resulting mixture was diluted with 60 ml of methylene chloride and washed with 100 ml of water. The organic phase was washed successively with two 100 ml portions of 25% potassium carbonate, and 100 ml of saturated sodium chloride, dried with MgSO4 and vacuum concentrated to leave 5.7 g of the desired product as an oil.

Workup

  1. temperatureA temperature increase from 20° C. to 37° C.
  2. customresulted
  3. temperatureThe resulting solution was refluxed for 1 hour
  4. washwashed with 100 ml of water
  5. washThe organic phase was washed successively with two 100 ml portions of 25% potassium carbonate, and 100 ml of saturated sodium chloride
  6. dry with materialdried with MgSO4 and vacuum
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7b3b770d27634f2996b5e138daa671d2
Source dataset
uspto-grants-1983_10
Patent number
US04410354

Reaction notes

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