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

HRID 1706877Notes

Reaction equation

HRID 1706877 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].O[CH2:13][CH:14]([OH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(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:21][CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][O:4]1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 71491-Phenyl-1,2-ethanediolHCID 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-9ece47b8fedc45b5becedd1191a53e72
Source dataset
uspto-grants-1980_06
Patent number
US04209447

Reaction notes

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