Propylene Glycol → 2-Chloromethyl-4-methyl-2-(2,5-dimethylphenyl)-[1,3]dioxolane

HRID 2106073Notes

Reaction equation

HRID 2106073 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)[CH:14]([OH:16])[CH3:15]>C1(C)C(C)=CC=CC=1>[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:16][CH:14]([CH3:15])[CH2:13][O:4]1

Participants

4

Reactant 2

HCID 1030Propylene GlycolHCID 23636932-Chloro-1-(2,5-dimethylphenyl)ethan-1-one

Product 1

HCID 578106322-Chloromethyl-4-methyl-2-(2,5-dimethylphenyl)-[1,3]dioxolane

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 36.5 g [0.2 mol] of 2-chloro-1-(2,5-dimethylphenyl)ethanone, 22.8 g [0.3 mol] of propylene glycol, 3.6 g [0.02 mol] of p-TsOH hydrate and 150 ml of xylene is heated to boiling with a water trap for about 1.5 hours. Part of the xylene is then distilled off, and the reaction mixture is extracted at room temperature twice with 100 ml of water each time. The organic phase is dried over sodium sulfate and concentrated in vacuo, and volatiles are distilled off up to about 50° C./0.2 mbar. 39.65 g of an orange-colored oil remain with, according to GC, 93.0% product (76.7% of theory).

Workup

  1. temperatureis heated
  2. distillationPart of the xylene is then distilled off
  3. extractionthe reaction mixture is extracted at room temperature twice with 100 ml of water each time
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationconcentrated in vacuo, and volatiles
  6. distillationare distilled off up to about 50° C./0.2 mbar

Sources & evidence

ORD record
ord-14ddfaa943ad47a889292f74f7d08974
Source dataset
uspto-grants-2009_08
Patent number
US07579500B2

Reaction notes

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