Ethylene Glycol → 2-(3-Chloropropyl)-2-(4-methylphenyl)-1,3-dioxolane

HRID 498150Notes

Reaction equation

HRID 498150 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)=[O:6].[CH2:14](O)[CH2:15][OH:16].C1(C)C=CC(S(O)(=O)=O)=CC=1.CCCCCCC.CCOCC>C1(C)C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1([C:7]2[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][CH:12]=2)[O:16][CH2:15][CH2:14][O:6]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 987454-Chloro-4'-methylbutyrophenoneHCID 21897273Diethylether heptane

Product 1

HCID 223208902-(3-Chloropropyl)-2-(4-methylphenyl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

This compound was synthesized as described under 5.a) with 20.0 g (101.6 mmol) of 4-chloro-1-(4-methylphenyl)-1-butanone (origin: Acros), 20 ml of ethylene glycol and ca. 1 g of p-toluenesulfonic acid in 120 ml of toluene to give 25.2 g (99%) of the crude compound, which was used for further functionalization. Column chromatography of 2 g (SiO2, heptane/ether 9:1) afforded 1.51 g of a yellow oil.

Workup

  1. customThis compound was synthesized
  2. customto give 25.2 g (99%) of the crude compound, which

Sources & evidence

ORD record
ord-cc60de79f4164b80956e1dad1b505011
Source dataset
uspto-grants-2005_09
Patent number
US06949680B2

Reaction notes

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