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

HRID 364620Notes

Reaction equation

HRID 364620 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([F: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.O>C1C=CC=CC=1>[CH2:15]1[O:16][C:5]([C:7]2[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=2)([CH2:4][CH2:3][CH2:2][Cl:1])[O:6][CH2:14]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 197503-(4-Fluorobenzoyl)propyl chloride

Product 1

HCID 27237782-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolaneYield 93%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of γ-chloro-p-fluorobutyrophenone (50 g, 0.25 mole, commercially available); ethylene glycol (50 mL); p-toluene sulfonic acid (0.1 g) in 300 mL benzene is refluxed for 18 hrs with water of reaction being removed by means of a Dean Stark water trap. Upon cooling to room temperature, the reaction mixture is washed with dilute sodium bicarbonate, dried (MgSO4), filtered and the benzene removed by concentration in vacuo. The residual oil was distilled to give 57.7 g (93%) of product, b.p. 106-112/0.01 Torr.

Workup

  1. custombeing removed by means of a Dean Stark water trap
  2. washthe reaction mixture is washed with dilute sodium bicarbonate
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe benzene removed by concentration in vacuo
  6. distillationThe residual oil was distilled

Sources & evidence

ORD record
ord-9e49b3713c6a484691aa8efd2532ca7c
Source dataset
uspto-grants-1986_08
Patent number
US04605655

Reaction notes

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