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

HRID 498147Notes

Reaction equation

HRID 498147 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:6].[CH2:15](O)[CH2:16][OH:17].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1.CCCCCCC.CCOCC.CCOCC>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1([C:7]2[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=2)[O:17][CH2:16][CH2:15][O:6]1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 964144-Chloro-4'-methoxybutyrophenone

Product 1

HCID 147641952-(3-Chloropropyl)-2-(4-methoxyphenyl)-1,3-dioxolane

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 21897273Diethylether heptaneSolvent

Procedure

A solution of 20.0 g (94.0 mmol) of 4-chloro-1-(4-methoxyphenyl)-1-butanone (origin: Acros), 19 ml of ethylene glycol and ca. 1 g of p-toluenesulfonic acid in 120 ml of toluene was heated under reflux with azeotropic removal of water for 16 h. After cooling down to room temperature, ether was added and the organic phase extracted with a saturated solution of NaHCO3 (2×), washed with water (2×), dried (Na2SO4) and concentrated in vacuo to give 24.6 g (99%) of the crude compound, which was used for further functionalization. Column chromatography of 2 g (SiO2, heptane/ether 9:1) afforded 1.15 g of a slightly yellow oil.

Workup

  1. extractionthe organic phase extracted with a saturated solution of NaHCO3 (2×)
  2. washwashed with water (2×)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give 24.6 g (99%) of the crude compound, which

Sources & evidence

ORD record
ord-a10a36fa93494a7e99844b2b70bae915
Source dataset
uspto-grants-2005_09
Patent number
US06949680B2

Reaction notes

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