1-Butanol → 2-(Bromomethyl)-2-(2,4-dichlorophenyl)-4-[2-(2,4-dichlorophenyl)ethyl]-1,3-dioxolane

HRID 1706894Notes

Reaction equation

HRID 1706894 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[Cl:12])=[O:4].[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[CH2:21][CH2:22][C:23](O)([OH:25])[CH3:24].CC1C=CC(S(O)(=O)=O)=CC=1.C(O)CCC>C1C=CC=CC=1>[Br:1][CH2:2][C:3]1([C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=2[Cl:12])[O:25][CH:23]([CH2:22][CH2:21][C:15]2[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:14]=2[Cl:13])[CH2:24][O:4]1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 6101p-Toluenesulfonic acidHCID 758282-Bromo-1-(2,4-dichlorophenyl)ethan-1-oneHCID 203326861-[2-(2,4-Dichlorophenyl)ethyl]ethanediol

Product 1

HCID 203327282-(Bromomethyl)-2-(2,4-dichlorophenyl)-4-[2-(2,4-dichlorophenyl)ethyl]-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 13.6 parts of 2-bromo-1-(2,4-dichlorophenyl)-1-ethanone, 14.1 parts of 1-[2-(2,4-dichlorophenyl)ethyl]ethanediol, 3 parts of 4-methylbenzenesulfonic acid, 80 parts of butanol and 180 parts of benzene is stirred and refluxed for 24 hours. The reaction mixture is evaporated and the residue is stirred for 2 hours with 160 parts of methanol. The precipitated product is filtered off, yielding 2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-[2-(2,4-dichlorophenyl)ethyl]-1,3-dioxolane.

Workup

  1. temperaturerefluxed for 24 hours
  2. customThe reaction mixture is evaporated
  3. stirringthe residue is stirred for 2 hours with 160 parts of methanol
  4. filtrationThe precipitated product is filtered off

Sources & evidence

ORD record
ord-ebb97d9110d8493785f40c825c80f670
Source dataset
uspto-grants-1980_06
Patent number
US04209447

Reaction notes

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