1-Butanol → HCID 20332621, compound

HRID 1390590Notes

Reaction equation

HRID 1390590 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]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[CH:20]([OH:23])[CH2:21]O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)CCC>O.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:23][CH:20]([C:14]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:13]=2[Cl:12])[CH2:21][O:4]1

Participants

7

Reactant 4

HCID 2631-ButanolHCID 6101p-Toluenesulfonic acidHCID 68303p-Chlorophenacyl bromideHCID 13084216(2,4-Dichlorophenyl)ethane-1,2-diol

Product 1

HCID 20332621HCID 20332621, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of 11.6 parts of 2-bromo-4'-chloroacetophenone, 12.4 parts of 1-(2,4-dichlorophenyl)-1,2-ethanediol, 0.1 parts of p-toluenesulfonic acid, 80 parts of n-butanol and 160 parts of benzene is stirred and refluxed for 24 hours with water-separator. The solvent is removed in vacuo and the residue is triturated in methanol. The precipitated product is filtered off and crystallized from petroleum ether, yielding 2-(bromomethyl)-2-(p-chlorophenyl)-4-(2,4-dichlorophenyl)-1,3-dioxolane; m.p. 82.7° C.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is triturated in methanol
  3. filtrationThe precipitated product is filtered off
  4. customcrystallized from petroleum ether

Sources & evidence

ORD record
ord-9d55873756714f1a85475a65cf763de8
Source dataset
uspto-grants-1979_02
Patent number
US04139540

Reaction notes

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