Benzene → HCID 20332642, compound

HRID 1390592Notes

Reaction equation

HRID 1390592 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:22]=[CH:21][CH:20]=[CH:19][C:14]=1[CH:15]([OH:18])[CH2:16]O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O.C(O)CCC>[Br:1][CH2:2][C:3]1([C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=2)[O:18][CH:15]([C:14]2[CH:19]=[CH:20][CH:21]=[CH:22][C:13]=2[Cl:12])[CH2:16][O:4]1

Participants

7

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 68303p-Chlorophenacyl bromideHCID 1010261-(2-Chlorophenyl)ethane-1,2-diol

Product 1

HCID 20332642HCID 20332642, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

A mixture of 11.5 parts of 2-bromo-p-chloroacetophenone, 10.4 parts of o-chloro-α-(hydroxymethyl)benzylalcohol, 0.2 parts of p-toluenesulfonic acid, 180 parts of benzene and 80 parts of butanol is stirred and refluxed overnight with water-separator. The solvent is removed in vacuo and the residue is dissolved in chloroform. The chloroform solution is stirred with silica gel for 30 minutes. The silica gel is filtered off and the solvent is removed in vacuo, yielding 2-(bromomethyl)-4-(o-chlorophenyl)-2-(p-chlorophenyl)-1,3-dioxolane as a residue.

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionthe residue is dissolved in chloroform
  3. stirringThe chloroform solution is stirred with silica gel for 30 minutes
  4. filtrationThe silica gel is filtered off
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-7e57010b10d642c28b08c0ce7837023e
Source dataset
uspto-grants-1979_02
Patent number
US04139540

Reaction notes

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