Ethylene Glycol → 2-Chloromethyl-2-(2,5-dimethylphenyl)-[1,3]dioxolane

HRID 2106071Notes

Reaction equation

HRID 2106071 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[CH3:12])=[O:4].[CH2:13](O)[CH2:14][OH:15].[Na+].[Cl-]>C1(C)C(C)=CC=CC=1.O>[Cl:1][CH2:2][C:3]1([C:5]2[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=2[CH3:12])[O:15][CH2:14][CH2:13][O:4]1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 5234Sodium ChlorideHCID 23636932-Chloro-1-(2,5-dimethylphenyl)ethan-1-one

Product 1

HCID 578106302-Chloromethyl-2-(2,5-dimethylphenyl)-[1,3]dioxolaneYield 80.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent2×

Procedure

A mixture of 18.3 g [0.1 mol] of 2-chloro-1-(2,5-dimethylphenyl)ethanone, 12.6 g [0.2 mol] of ethylene glycol, 1.9 g [0.01 mol] of p-TsOH hydrate and 100 ml of xylene is heated to boiling with a water trap for about 3 hours. 40 ml of water and 20 ml of saturated aqueous NaCl solution are then added to the reaction mixture at room temperature. After addition of 20 ml of xylene, the organic phase is separated off and extracted with 20 ml each of water and saturated aqueous NaCl solution. The organic phase is dried over sodium sulfate and concentrated in vacuo. 18.35 g of oil result with, according to GC, 95.3% product (77.2% of theory).

Workup

  1. temperatureis heated
  2. customthe organic phase is separated off
  3. extractionextracted with 20 ml each of water and saturated aqueous NaCl solution
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5ea2f9015cce428f8af02d9994499083
Source dataset
uspto-grants-2009_08
Patent number
US07579500B2

Reaction notes

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