Glycerol → HCID 14872530, compound

HRID 440835Notes

Reaction equation

HRID 440835 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=[O:4].[OH:12][CH2:13][CH:14]([CH2:16]O)[OH:15].CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>CC1C=CC=CC=1.O>[Br:1][CH2:2][C:3]1([C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=2)[O:15][CH:14]([CH2:13][OH:12])[CH2:16][O:4]1

Participants

7

Reactant 4

HCID 753GlycerolHCID 6101p-Toluenesulfonic acidHCID 68303p-Chlorophenacyl bromideHCID 516892Sodium Bicarbonate

Product 1

HCID 14872530HCID 14872530, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 2-bromo-1-(4-chlorophenyl)ethanone (1.47 mol), glycerine (3.5 mol) and 4-methylbenzenesulfonic acid (0.25 mol) in methylbenzene (3000 ml) was stirred and refluxed for 24 hours, using a water separator. The reaction mixture was poured out into an aqueous NaHCO3 solution and stirred for a while. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 485 g (93%; oil) of (cis +trans)-2-(bromomethyl)-2-(4-chlorophenyl)-1,3-dioxolane-4-methanol (interm. 8a).

Workup

  1. temperaturerefluxed for 24 hours
  2. stirringstirred for a while
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f1abc8bf4aed4e4f9a565ceceac33e8b
Source dataset
uspto-grants-1996_05
Patent number
US05521186

Reaction notes

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