p-Toluenesulfonic acid → 2-(Bromomethyl)-4-[(4-chlorophenoxy)methyl]-2-(4-chlorophenyl)-1,3-dioxolane

HRID 1578433Notes

Reaction equation

HRID 1578433 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].[Cl:12][C:13]1[CH:24]=[CH:23][C:16]([O:17][CH2:18][CH:19]([OH:22])[CH2:20]O)=[CH:15][CH:14]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Br:1][CH2:2][C:3]1([C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=2)[O:22][CH:19]([CH2:18][O:17][C:16]2[CH:15]=[CH:14][C:13]([Cl:12])=[CH:24][CH:23]=2)[CH2:20][O:4]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7697ChlorphenesinHCID 68303p-Chlorophenacyl bromide

Product 1

HCID 203326492-(Bromomethyl)-4-[(4-chlorophenoxy)methyl]-2-(4-chlorophenyl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 11.7 parts of 2-bromo-4'-chloroacetophenone, 12.2 parts of 1-(p-chlorophenoxy)-2,3-propanediol, 3 parts of p-toluenesulfonic acid and 240 parts of benzene is stirred and refluxed for 20 hours in a four-necked round-bottom flask equipped with a watertrap. The benzene solution is washed successively with a diluted sodium hydroxide solution and with water. The solvent is removed in vacuo. The residue is triturated in methanol. The precipitated product is filtered off (methanol filtrate is set aside) and crystallized from toluene, yielding A-2-(bromomethyl-4-(p-chlorophenoxymethyl)-2-(p-chlorophenyl)-1,3-dioxolane; m.p. 165°C.

Workup

  1. temperaturerefluxed for 20 hours in a four-necked round-bottom flask
  2. customequipped with a watertrap
  3. washThe benzene solution is washed successively with a diluted sodium hydroxide solution and with water
  4. customThe solvent is removed in vacuo
  5. customThe residue is triturated in methanol
  6. filtrationThe precipitated product is filtered off (methanol filtrate
  7. customcrystallized from toluene

Sources & evidence

ORD record
ord-ed4f67585ce84caeb44a058025c132e3
Source dataset
uspto-grants-1976_02
Patent number
US03936470

Reaction notes

Loading…