m-Chloroperbenzoic acid → (2-Ethyl-1,7,10-trioxaspiro[4.6]undecan-2-yl)methanol

HRID 647745Notes

Reaction equation

HRID 647745 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]=[C:13]([CH2:24][CH3:25])[CH2:14][CH2:15][C:16]1([OH:23])[CH2:22][O:21][CH2:20][CH2:19][O:18][CH2:17]1>C(Cl)Cl>[CH2:24]([C:13]1([CH2:12][OH:9])[CH2:14][CH2:15][C:16]2([CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22]2)[O:23]1)[CH3:25]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 132371746-(3-Methylidenepentyl)-1,4-dioxepan-6-ol

Product 1

HCID 13237163(2-Ethyl-1,7,10-trioxaspiro[4.6]undecan-2-yl)methanolYield 63.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3.22 g of 3-chloroperbenzoic acid dissolved in 20 ml of methylene chloride under nitrogen, was added dropwise 3.05 g of tetrahydro-6-(3-methylenepentyl)-1,4-dioxepin-6-ol while maintaining the temperature below 30° C. using a water bath. After six hours and 20 minutes, the reaction mixture was washed with a 25% solution of potassium carbonate and a saturated sodium chloride solution, dried and stripped to yield 2.10 g of the desired product as a dark brown liquid.

Workup

  1. temperaturewhile maintaining the temperature below 30° C.
  2. wash20 minutes, the reaction mixture was washed with a 25% solution of potassium carbonate
  3. dry with materiala saturated sodium chloride solution, dried

Sources & evidence

ORD record
ord-103510cf4a2c4c55975a3bbf649e9e9a
Source dataset
uspto-grants-1983_10
Patent number
US04410354

Reaction notes

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