1,1-Ethanediol → 2-(3-Chloropropyl)-2-phenyl-1,3-dioxolane

HRID 1585649Notes

Reaction equation

HRID 1585649 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[CH:13](O)([OH:15])[CH3:14]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:7]1([C:5]2([CH2:4][CH2:3][CH2:2][Cl:1])[O:15][CH2:13][CH2:14][O:6]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 1512111,1-EthanediolHCID 2535334-Chlorobutyrophenone

Product 1

HCID 128663382-(3-Chloropropyl)-2-phenyl-1,3-dioxolaneYield 111.6%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

4-Chlorobutyrophenone (15.18 g, 0.083 moles), ethanediol (6.80 g, 0.110 moles) and p-toluene sulphonic acid (0.20 g) were heated in toluene at reflux and water was removed from the reaction using a Dean and Stark apparatus. After 17 hours the solvent was removed by distillation in vacuo to leave crude 2-phenyl-2-(3-chloropropyl)-1,3-dioxolane (21 g).

Workup

  1. temperatureat reflux
  2. customwater was removed from the reaction
  3. customAfter 17 hours the solvent was removed by distillation in vacuo

Sources & evidence

ORD record
ord-3d2fcc7e27644a48bc71b43e6a7389cd
Source dataset
uspto-grants-1999_08
Patent number
US05939447

Reaction notes

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