Benzene → 2-(Bromomethyl)-2-(4-chlorophenyl)-4-phenyl-1,3-dioxolane

HRID 1578429Notes

Reaction equation

HRID 1578429 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].[CH2:12]([OH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:20]1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>C(O)C>[Br:1][CH2:2][C:3]1([C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=2)[O:19][CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:20][O:4]1

Participants

6

Reactant 4

HCID 241BenzeneHCID 244Benzyl AlcoholHCID 6101p-Toluenesulfonic acidHCID 68303p-Chlorophenacyl bromide

Product 1

HCID 203326352-(Bromomethyl)-2-(4-chlorophenyl)-4-phenyl-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 11.6 parts of 2-bromo-4'-chloroacetophenone, 8.4 parts of α-hydroxymethyl)benzylalcohol, 0.1 parts of p-toluene sulfonic acid, 210 parts of benzene and 40 parts of ethanol is stirred and refluxed for 24 hours. The reaction mixture is evaporated and the residue is triturated in methanol. The product is filtered off and crystallized from methanol, yielding 2-(bromomethyl)-2-(p-chlorophenyl)-4-phenyl-1,3-dioxolane; mp. 60°C.

Workup

  1. temperaturerefluxed for 24 hours
  2. customThe reaction mixture is evaporated
  3. customthe residue is triturated in methanol
  4. filtrationThe product is filtered off
  5. customcrystallized from methanol

Sources & evidence

ORD record
ord-14348282bbdc4d70a9d6a67071fa6ef3
Source dataset
uspto-grants-1976_02
Patent number
US03936470

Reaction notes

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