p-Toluenesulfonic acid → HCID 86733043, compound

HRID 1578432Notes

Reaction equation

HRID 1578432 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:18]=[CH:17][C:16]([CH3:19])=[C:15]([O:20][CH2:21][CH:22]([OH:25])[CH2:23]O)[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:25][CH:22]([CH2:21][O:20][C:15]2[CH:14]=[C:13]([Cl:12])[CH:18]=[CH:17][C:16]=2[CH3:19])[CH2:23][O:4]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 68303p-Chlorophenacyl bromideHCID 21423644HCID 21423644, compound

Product 1

HCID 86733043HCID 86733043, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 11.7 parts of 2-bromo-4'-chloroacetophenone, 11.9 parts of 1-(4-chloro-o-tolyloxy)-2,3-propanediol, 2.5 parts of p-toluenesulfonic acid and 240 parts of benzene is stirred and refluxed for 24 hours in a four-necked round-bottomed 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 crystallized from methanol and the less pure fraction is recrystallized from diisopropylether, yielding A-2-(bromomethyl-2-(p-chlorophenyl)-4-(4-chloro-o-tolyloxymethyl)-1,3-dioxolane; m.p. 102.5°C. The methanol filtrate is evaporated in vacuo, yielding B-2-(bromomethyl)-2-(p-chlorophenyl)-4-(4-chloro-o-tolyloxymethyl)-1,3-dioxolane as a residue.

Workup

  1. temperaturerefluxed for 24 hours in a four-necked round-bottomed 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 crystallized from methanol
  6. customthe less pure fraction is recrystallized from diisopropylether

Sources & evidence

ORD record
ord-d6fd96f965144fd4b75cc59f01c24fef
Source dataset
uspto-grants-1976_02
Patent number
US03936470

Reaction notes

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