m-Chloroperbenzoic acid → 5,7-Dimethyl-4-hydroxy-6,8-dioxabicyclo(3.2.1)octane

HRID 2166650Notes

Reaction equation

HRID 2166650 reaction equation
[OH:1][CH:2]([CH:4]1[CH2:9][CH2:8][CH:7]=[C:6]([CH3:10])[O:5]1)[CH3:3].ClC1C=C(C=CC=1)C(OO)=[O:16]>C(Cl)Cl>[CH3:10][C:6]12[O:5][CH:4]([CH:2]([CH3:3])[O:1]1)[CH2:9][CH2:8][CH:7]2[OH:16]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 3323121-(6-methyl-3,4-dihydro-2H-pyran-2-yl)ethanol

Product 1

HCID 204982715,7-Dimethyl-4-hydroxy-6,8-dioxabicyclo(3.2.1)octane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 11.60 g of 16B in 25 ml of methylene chloride was added drop by drop to a stirred solution of 16.44 g of m-chloroperoxybenzoic acid in 150 ml of methylene chloride under a nitrogen atmosphere at 3° C.±10° C. The mixture was allowed to warm to room temperature and after 2 hours was washed with 800 ml of 25% aqueous potassium carbonate solution and saturated aqueous sodium chloride solution, dried (MgSO4) and stripped of solvent. The residue was chromatographed (high pressure liquid) over silica gel, using in sequence one liter each of six liquids: hexane, and five mixtures of ethyl acetate and hexane, as eluents, the volume ratios of the two components in the mixtures being, respectively: 210/790; 400/600; 400/600; 560/440; 800/200. One set of fractions was collected and stripped of solvent to give 5,7-dimethyl-4-hydroxy-6,8-dioxabicyclo(3.2.1)octane (18A), as a liquid, b.p.: not determined.

Workup

  1. washwas washed with 800 ml of 25% aqueous potassium carbonate solution and saturated aqueous sodium chloride solution
  2. dry with materialdried (MgSO4)
  3. customThe residue was chromatographed (high pressure liquid) over silica gel
  4. customOne set of fractions was collected

Sources & evidence

ORD record
ord-6a8954b477874aaf87ec0fd0e1100b5d
Source dataset
uspto-grants-1983_06
Patent number
US04388104

Reaction notes

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