Acetone → HCID 21461387, compound

HRID 1941518Notes

Reaction equation

HRID 1941518 reaction equation
[Br:1][CH2:2][CH:3]1[O:9][CH2:8][CH:7]([OH:10])[CH:6]([OH:11])[CH2:5][O:4]1.[CH3:12][C:13]([CH3:15])=O>C1(C)C=CC(S(O)(=O)=O)=CC=1.C(Cl)Cl>[Br:1][CH2:2][CH:3]1[O:4][CH2:5][CH:6]2[CH:7]([O:10][C:13]([CH3:15])([CH3:12])[O:11]2)[CH2:8][O:9]1

Participants

5

Reactant 2

HCID 180AcetoneHCID 21461382HCID 21461382, compound2×

Product 1

HCID 21461387HCID 21461387, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.93 mol (211 g) of 2-bromomethyl-5,6-dihydroxy-1,3-dioxepane, 5.75 mol (422 ml) of acetone, 1.8 g of p-toluenesulphonic acid and 750 ml of methylene chloride was heated under reflux and the water formed was separated by means of a water separator. After about 9 h, the methylene chloride was drawn off in the rotary evaporator (filter pump), and the residue underwent fractional distillation under a medium high vacuum. At 89°-92° C. (0.5 mbar), 231 g of 4-bromomethyl-9,9-dimethyl-3,5,8,10-tetraoxabicyclo[5,3,0]decane (93% yield) were obtained as a colourless liquid which exhibited crystalline deposits in some cases at room temperature and was a mixture of isomers.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customwas separated by means of a water separator
  4. customthe methylene chloride was drawn off in the rotary evaporator (filter pump)
  5. distillationthe residue underwent fractional distillation under a medium high vacuum

Sources & evidence

ORD record
ord-d286b095a2fc4d46964d1d8c82d9d6ce
Source dataset
uspto-grants-1997_12
Patent number
US05703249

Reaction notes

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