Ethylene Glycol → 2-(4-Tert-butylphenyl)-2-(3-chloropropyl)-1,3-dioxolane

HRID 498153Notes

Reaction equation

HRID 498153 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:16])[CH2:12][CH2:13][CH2:14][Cl:15])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:17](O)[CH2:18][OH:19].C1(C)C=CC(S(O)(=O)=O)=CC=1.CCCCCCC.CCOCC>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2([CH2:12][CH2:13][CH2:14][Cl:15])[O:19][CH2:18][CH2:17][O:16]2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 27236944'-tert-Butyl-4-chlorobutyrophenoneHCID 21897273Diethylether heptane

Product 1

HCID 223209002-(4-Tert-butylphenyl)-2-(3-chloropropyl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

This compound was synthesized as described under 5.a) with 20.0 g (83.8 mmol) of 1-(4-tert-butylphenyl)-4-chloro-1-butanone (origin: Acros), 16 ml of ethylene glycol and ca. 1 g of p-toluenesulfonic acid in 120 ml of toluene for 16 h to give 24.1 g (99%) of the crude compound, which was used for further functionalization. Column chromatography of 3 g (SiO2, heptane/ether 4:1) afforded 2.48 g of a slightly yellow oil.

Workup

  1. customThis compound was synthesized
  2. customfor 16 h
  3. customto give 24.1 g (99%) of the crude compound, which

Sources & evidence

ORD record
ord-1364835ed6ea41f380a92199589e008c
Source dataset
uspto-grants-2005_09
Patent number
US06949680B2

Reaction notes

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