Peracetic Acid → (2-Ethyl-1,8-dioxaspiro[4.5]decan-2-yl)methanol

HRID 647747Notes

Reaction equation

HRID 647747 reaction equation
[CH2:1]=[C:2]([CH2:12][CH3:13])[CH2:3][CH2:4][C:5]1([OH:11])[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.C(OO)(=[O:16])C>C(Cl)Cl>[CH2:12]([C:2]1([CH2:1][OH:16])[CH2:3][CH2:4][C:5]2([CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[O:11]1)[CH3:13]

Participants

4

Reactant 2

HCID 6585Peracetic AcidHCID 132371754-(3-Methylidenepentyl)oxan-4-ol

Product 1

HCID 13237164(2-Ethyl-1,8-dioxaspiro[4.5]decan-2-yl)methanolYield 69.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 16.52 g of tetrahydro-4-(3-methylenepentyl)-2H-pyran-4-ol in 100 ml of methylene chloride under nitrogen was added portionwise 15.32 g of peracetic acid (with 0.40 g of anhydrous sodium acetate added). The reaction mixture was refluxed for 1 hour, allowed to set for 4 hours, diluted with 150 ml of methylene chloride, washed successively with water, twice with 25% potassium carbonate, and saturated sodium chloride, dried and filtered. The resulting solution was stripped to yield 12.42 g of the desired product as a pale yellow liquid.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. washwashed successively with water, twice with 25% potassium carbonate, and saturated sodium chloride
  3. customdried
  4. filtrationfiltered

Sources & evidence

ORD record
ord-0fded67d8f374b2bb173593a462c50d1
Source dataset
uspto-grants-1983_10
Patent number
US04410354

Reaction notes

Loading…